1-Bromo-3-chloropropane → HCID 14526712, compound

HRID 2287635Notes

Reaction equation

HRID 2287635 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].[Na].Br[CH2:10][CH2:11][CH2:12][Cl:13]>C1(C)C(C)=CC=CC=1>[Cl:13][CH2:12][CH2:11][CH2:10][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 126652-PiperidoneHCID 5360545Sodium

Product 1

HCID 14526712HCID 14526712, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-piperidone (1.19 g, 12.0 mmcl) and finely pulverized sodium metal (0.28 g, 12.0 mmol) in dry xylene (70 ml) was heated at 110° C. with vigrous stirring, 1-bromo-3-chloropropane (1.89 g, 12.0 mmol) was added to the stirred reaction mixture after 3 hours and the heating at 110° C. was continued for 6 hours. The reaction mixture was filtered and xylene was removed under reduced pressure. The residue was chromatographed on silica gel using hexane and chloroform as eluant to get 3 (n=2), B.P. 91° C./0.01 mm., yield 1.33 g (63.33%). IR (Neat): 3862, 3298, 2950, 2474, 2324, 1640, 1478, 1432, 1336, 1184, 1096, 754. 1H NMR (CDCl3): 1.79-2.36(m,8H), 3.15-3.67(m,6H). MS: m/z 175 (M+).

Workup

  1. additionwas added to the stirred reaction mixture after 3 hours
  2. filtrationThe reaction mixture was filtered
  3. customxylene was removed under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. customto get 3 (n=2), B.P. 91° C./0.01 mm

Sources & evidence

ORD record
ord-831e2734f9d0468aba9eca470e6e3cd3
Source dataset
uspto-grants-2000_07
Patent number
US06084097

Reaction notes

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