epsilon-CAPROLACTONE → 1-Nonylazepan-2-one

Reaction equation

[C:1]1(=O)[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>>[CH2:10]([N:9]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[O:7])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 2

HCID 10401epsilon-CAPROLACTONE

HCID 16215Nonylamine

Product 1

HCID 128332631-Nonylazepan-2-oneYield 26%

Procedure

Following example 5, heating 22.83 g (0.2 M) of 6-hexanolactone and 28.65 g (0.2 M) of 1-aminononane at 180° for 20 hours gave 11.5 g (26%) of product; b.p. 155°-165°/0.6 mm.

Sources & evidence

ORD record: ord-c410ea8fff1b4bf99f344b35b515d40e
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415563

Reaction notes

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