Caprolactam → 1-Decylazepan-2-one

HRID 326073Notes

Reaction equation

HRID 326073 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][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[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][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 7768CaprolactamHCID 81731-BromodecaneHCID 24758Sodium hydride2×

Product 1

HCID 128332641-Decylazepan-2-oneYield 84.8%

Procedure

Following example 10, 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 44.2 g (0.2 M) of 1-bromodecane on 19 hr. reflux gave 38 g (84.7%) of product; b.p. 158°-163°/0.25-0.3 mm.

Workup

  1. customon 19 hr
  2. temperaturereflux

Sources & evidence

ORD record
ord-f049aeaebe694ddf8f5f4773d0de44d7
Source dataset
uspto-grants-1984_04
Patent number
US04444762

Reaction notes

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