Caprolactam → 1-Pentylazepan-2-one

HRID 326068Notes

Reaction equation

HRID 326068 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][CH3:16]>>[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][CH3:16]

Participants

4

Reactant 3

HCID 7768CaprolactamHCID 80571-BromopentaneHCID 24758Sodium hydride2×

Product 1

HCID 128332611-Pentylazepan-2-oneYield 87%

Procedure

Following example 8 and using water condenser from the start of the reaction, 10 g of 50% sodium hydride-mineral oil dispersion (5 g NaH, 0.21 M), 20 g (0.177 M) of azacycloheptan-2-one and 30.2 g (0.2 M) of 1-bromopentane on 18 hr. reflux gave 23.3 g (87%) of colorless product; b.p. 110°-115°/0.3 mm.

Workup

  1. temperaturereflux

Sources & evidence

ORD record
ord-d772fd4a24d5442f84e803b21de08f44
Source dataset
uspto-grants-1984_04
Patent number
US04444762

Reaction notes

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