1-Bromo-3-chloropropane → HCID 10460436, compound

HRID 852292Notes

Reaction equation

HRID 852292 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:8](=[O:21])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH:30]1[CH2:34][CH2:33][CH2:32][C:31]1=[O:35].Br[CH2:37][CH2:38][CH2:39][Cl:40]>>[ClH:40].[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]([CH:22]2[CH2:27][CH2:26][N:25]([CH2:37][CH2:38][CH2:39][N:30]3[CH2:34][CH2:33][CH2:32][C:31]3=[O:35])[CH2:24][CH2:23]2)[C:8](=[O:21])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 120252-PyrrolidoneHCID 10097003HCID 10097003, compound

Product 1

HCID 10460436HCID 10460436, compoundYield 11%

Procedure

The desired compound was synthesized from N-(4-fluorobenzyl)-2-(4-isobutoxyphenyl)-N-piperidin-4-yl-acetamide 103NLS56 (107 mg, 0.27 mmol), 2-pyrrolidone and 1-bromo-3-chloropropane using the same method as for synthesis of 98AF73-64. Purification of the product by silica gel column chromatography, eluting with a stepwise gradient of 4–8% methanol in dichloromethane; afforded the title compound (15 mg, 11%).

Workup

  1. customas for synthesis of 98AF73-64
  2. customPurification of the product by silica gel column chromatography
  3. washeluting with a stepwise gradient of 4–8% methanol in dichloromethane

Sources & evidence

ORD record
ord-0be6e7b0ba2b452980957d803912e0c8
Source dataset
uspto-grants-2007_08
Patent number
US07253186B2

Reaction notes

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