2-piperazin-2-ylethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966).) To 25.0 g (0.192 mol) of 2-(2-hydroxyethyl)piperazine, chilled in dry ice, 125 ml SOCl2 was cautiously added dropwise. After addition was complete, the mixture was cautiously heated on a steam bath with stirring for 2 hr. The reaction was cooled and treated cautiously with H2O until a solution resulted. The reaction was evaporated to dryness, and the dark residue was redissolved in H2O and filtered. The dark filtrate was heated on the steam bath with decolorizing carbon for 30 min and filtered to yield a pale yellow solution. Acetone was added to precipitate the product in two crops: 29.3 g white solid, mp 336°-339° dec., and 11.6 g (total 96% yield) pale-yellow solid, mp 330°-350° dec. (E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966) mp 348°-350° dec.) After addition the mixture was cautiously heated on a steam bath The reaction was cooled resulted The reaction was evaporated to dryness the dark residue was redissolved in H2O filtered The dark filtrate was heated on the steam bath with decolorizing carbon for 30 min filtered to yield a pale yellow solution to precipitate the product in two crops

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966).) To 25.0 g (0.192 mol) of 2-(2-hydroxyethyl)piperazine, chilled in dry ice, 125 ml SOCl2 was cautiously added dropwise. After addition was complete, the mixture was cautiously heated on a steam bath with stirring for 2 hr. The reaction was cooled and treated cautiously with H2O until a solution resulted. The reaction was evaporated to dryness, and the dark residue was redissolved in H2O and filtered. The dark filtrate was heated on the steam bath with decolorizing carbon for 30 min and filtered to yield a pale yellow solution. Acetone was added to precipitate the product in two crops: 29.3 g white solid, mp 336°-339° dec., and 11.6 g (total 96% yield) pale-yellow solid, mp 330°-350° dec. (E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966) mp 348°-350° dec.) After addition the mixture was cautiously heated on a steam bath The reaction was cooled resulted The reaction was evaporated to dryness the dark residue was redissolved in H2O filtered The dark filtrate was heated on the steam bath with decolorizing carbon for 30 min filtered to yield a pale yellow solution to precipitate the product in two crops

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A method for preparing each of the foregoing compounds is presented in the following examples. In general, however, the preparation is one wherein 2-(2-hydroxyethyl)-pyrazine (L. J. Kitchen and E. S. Hanson, Antibiot. Chemo., 73, 1838 (1951)) was reduced with H2 and PtO2 in MeOH to yield 2-(2-hydroxyethyl)piperazine (E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966)) which, in turn, was converted to the chloride. Ring closure in base afforded 1,4-diazabicyclo[ 3.2.1]octane which was acylated with ethylchloroformate to give 4-carbethoxy-1,4-diazabicyclo[ 3.2.1] octane or with diethylcarbamyl chloride to give 4-diethylcarbamyl-1,4-diazabicyclo[ 3.2.1] octane. A method for preparing each of the foregoing compounds

Conditions: temp:0.00; pressure:0.00; stir: