Lauric Acid → Hexahydro-1-lauroyl-1H-azepine

HRID 1904182Notes

Reaction equation

HRID 1904182 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(OC(=O)C)(=O)C.[NH:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)(=O)C>[C:1]([N:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 3893Lauric AcidHCID 7918Acetic AnhydrideHCID 8119Azepane

Product 1

HCID 96224Hexahydro-1-lauroyl-1H-azepineYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of dodecanoic acid (20.03 g, 0.1M), acetic anhydride (13.27 g, 0.13M), hexahydro-1H-azepine (12.9 g, 0.13M) was heated with distillation of formed acetic acid. The residue on distillation gave 23.46 g (83.5%) of colorless product, b.p. 204-205/7 mm.

Workup

  1. distillationThe residue on distillation

Sources & evidence

ORD record
ord-651a80f6587842b081a78181acadd43f
Source dataset
uspto-grants-1989_06
Patent number
US04837026

Reaction notes

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