Potassium Carbonate → HCID 52917912, compound

HRID 253083Notes

Reaction equation

HRID 253083 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C@H:9]1[C@H:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:13][CH2:12][NH:11][CH2:10]1.Br[CH2:32][C:33]#[N:34].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:28][C:25]([F:26])([F:27])[C:23]1[CH:22]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:24]=1)[CH2:6][O:7][CH2:8][C@H:9]1[C@H:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:13][CH2:12][N:11]([CH2:32][C:33]#[N:34])[CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 16747665HCID 16747665, compound

Product 1

HCID 52917912HCID 52917912, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (−)-(3S,4R)-3-(3,5-bis-trifluoromethyl-benzyloxymethyl)-4-(4-fluoro-phenyl)-piperidine (150 mg, 0.345 mmol), bromoacetonitrile (45 mg, 0.37 mmol) and potassium carbonate (95 mg, 0.69 mmol) in 4 ml of acetonitrile was stirred at room temperature over night. Quenching with water was followed by extraction with three portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 163 mg (99.7%) of the title compound as a white solid.

Workup

  1. customQuenching with water
  2. extractionwas followed by extraction with three portions of tert-butyl methyl ether
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6fcd4a0dbbc471c979d45e12e555834
Source dataset
uspto-grants-2011_01
Patent number
US07872022B2

Reaction notes

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