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

HRID 1857948Notes

Reaction equation

HRID 1857948 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 fnely 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 usinq 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 usinq hexane and chloroform as eluant
  5. customto get 3 (n=2), B.P. 91° C./0.01 mm

Sources & evidence

ORD record
ord-4919aa92d13e4b7aaaa88c97b7accb95
Source dataset
uspto-grants-2000_11
Patent number
US06150367

Reaction notes

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