cyclohexyl N-phenylcarbamate

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

Procedure: A mixture of 21.9 g. (0.10 mole) of cyclohexyl carbanilate, 100 ml. of 2-propanol, and 2.4 g. of 5% Rh on carbon was added to a 300-ml. Magne Drive autoclave. The vessel was sealed, purged first with nitrogen and then with hydrogen, and pressured with hydrogen to 700 psig. The autoclave was agitated at 25° and 500-800 psig for 0.4 hr., followed by an additional 0.9 hr. with little or no gas absorption. The autoclave was cooled and depressurized. The reaction product was removed and filtered through Celite filter aid to remove the catalyst. The solvent was removed in a rotary evaporator under vacuum. The white solid residue consisted of 21.9 g. (97% yield) of cyclohexyl cyclohexylcarbamate, m.p. 77°-78°. A mixture of 21.9 g The vessel was sealed purged first with nitrogen , followed by an additional 0.9 hr with little or no gas absorption The autoclave was cooled The reaction product was removed filtered through Celite filter aid to remove the catalyst The solvent was removed in a rotary evaporator under vacuum

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

Procedure: A mixture of 21.9 g. (0.10 mole) of cyclohexyl carbanilate, 77 ml. of 2-propanol, and 3.0 g. of 5% on carbon was added to a 0.5-1., glass, low pressure, Parr (trademark) shaker bottle. The apparatus was assembled, purged first with nitrogen and then with hydrogen, and pressured with hydrogen to 50 psig. The reaction mixture was agitated at room temperature and 50 to 25 psig for 3.0 hr., followed by an additional 0.8 hr. with little or no gas absorption. The reaction product was filtered through Celite filter aid to remove the catalyst. The solvent was removed in a rotary evaporator under vacuum. The solid residue consisted of 22.3 g. (99% yield) of cyclohexyl cyclohexylcarbamate, m.p. 77°-78°. Anal. Calcd. for C13H23NO2 : C, 69.29; H, 10.30; N, 6.21. Found: C, 69.43; H, 10.10; N, 6.20. A mixture of 21.9 g of 5% on carbon was added to a 0.5-1 purged first with nitrogen , followed by an additional 0.8 hr with little or no gas absorption The reaction product was filtered through Celite filter aid to remove the catalyst The solvent was removed in a rotary evaporator under vacuum