Caprolactam → 1-Hexylazepan-2-one

HRID 1447386Notes

Reaction equation

HRID 1447386 reaction equation
[H-].[Na+].[NH:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:10].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[CH2:12]([N:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 7768CaprolactamHCID 81011-BromohexaneHCID 24758Sodium hydride2×

Product 1

HCID 1815371-Hexylazepan-2-oneYield 85.4%

Procedure

Following example 10, from 10.2 g of 50% sodium hydride-mineral oil dispersion (5.1 g NaH, 0.2125 M), 20 g (0.177 M) of azacycloheptan-2-one and 33 g (0.2 M) of 1-bromohexane on 19 hr. reflux was obtained 29.8 g (85.3%) of colorless product; b.p 122-128°/0.4 mm.

Workup

  1. temperaturereflux

Sources & evidence

ORD record
ord-eff9ec46c3de4763afb09790773268da
Source dataset
uspto-grants-1982_02
Patent number
US04316893

Reaction notes

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