Chlorobenzene → Enclomiphene

HRID 1486465Notes

Reaction equation

HRID 1486465 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16](/[Cl:23])\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)[CH2:4][CH3:5].C(C(O)(C(O)=O)CC(O)=O)C(O)=O.ClC1C=CC=CC=1.[OH-].[Na+]>O>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16](/[Cl:23])\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 14798Sodium HydroxideHCID 6420009Enclomiphene citrate

Product 1

HCID 1548953Enclomiphene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round bottomed flask with standard equipment was loaded with 14.7 g of clomiphene citrate, 50 mL of chlorobenzene and 50 mL of water. Into the flask, 8 mL of aqueous sodium hydroxide 30% w/w were dropped, up to pH 12. The reaction mixture was stirred, the layers were separated, the organic phase was washed with 3 x 20 mL of water and treated with sodium sulfate, obtaining a clear solution of Clomiphene in chlorobenzene.

Workup

  1. customthe layers were separated
  2. washthe organic phase was washed with 3 x 20 mL of water
  3. additiontreated with sodium sulfate

Sources & evidence

ORD record
ord-7e6b4143851d45778750812ea744ec3d
Source dataset
uspto-grants-2016_08
Patent number
US09428442B2

Reaction notes

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