2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylmethanamine

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

Procedure: A mixture of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene- 5-methylamine (20.0 g), 5-chlorovaleric acid chloride (19.2 g) and sodium carbonate (35.0 g) in 250 ml of benzene is stirred and subjected to reflux for 16 hours. The reaction mixture is diluted with water. The benzene layer is separated and washed with water, dried and evaporated to dryness. The residue is crystallized from benzene-hexane to afford the haloamide N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-5- chlorovaleramide (III, Alk = CH2CH2CH2CH2 and Y = Cl), m.p. 98°-99° C. to reflux for 16 hours The benzene layer is separated washed with water dried evaporated to dryness The residue is crystallized from benzene-hexane

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

Procedure: A mixture of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-methylamine (20.0 g), 5-chlorovaleric acid chloride (19.2 g) and sodium carbonate (35.0 g) in 250 ml of benzene is stirred and subjected to reflux for 16 hours. The reaction mixture is diluted with water. The benzene layer is separated and washed with water, dried and evaporated to dryness The residue is crystallized from benzene-hexane to afford the haloamide N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-5-chlorovaleramide (III, Alk = CH2CH2CH2CH2 and Y = Cl), m.p.., 98°-99° C. to reflux for 16 hours The benzene layer is separated washed with water dried evaporated to dryness The residue is crystallized from benzene-hexane

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

Procedure: 10,11-Dihydro-5H-dibenzo[a,d]cycloheptene-5-methylamine (8.5 g) and γ-butyrolactone (3.7 g) are heated at 150° C. (internal temperature) for 1 hour. After cooling, the solid residue is recrystallized from benzene to give N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-hydroxybutyramide, (III, Alk = CH2CH2CH2 and Y = OH), m.p. 103°-105° C. After cooling the solid residue is recrystallized from benzene

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

Procedure: A mixture of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene- 5-methylamine (20.0 g), 5-chlorovaleric acid chloride (19.2 g) and sodium carbonate (35.0 g) in 250 ml of benzene is stirred and subjected to reflux for 16 hours. The reaction mixture is diluted with water. The benzene layer is separated and washed with water, dried and evaporated to dryness. The residue is crystallized from benzene-hexane to afford the haloamide N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-5- chlorovaleramide (III, Alk = CH2CH2CH2CH2 and Y = Cl), m.p. 98°-99° C. to reflux for 16 hours The benzene layer is separated washed with water dried evaporated to dryness The residue is crystallized from benzene-hexane