Potassium Hydroxide → HCID 9846525, compound

HRID 1420781Notes

Reaction equation

HRID 1420781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][O:6][CH:7]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]#[N:16])[CH2:8]1.[OH-:32].[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][O:6][CH:7]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]([NH2:16])=[O:32])[CH2:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11048281HCID 11048281, compound

Product 1

HCID 9846525HCID 9846525, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 1.80 g of 4-[3-(3-chlorobenzyloxy)pyrrolidine-1-yl]2,2-diphenylbutyronitrile was added 1.41 g of potassium hydroxide and 15 ml of tert-butanol, and the mixture was refluxed for 48 hours. The reaction mixture was poured into ice water, then extracted with methylene chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1) to obtain 1.57 g of the aimed compound as a yellow oil.

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. extractionextracted with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-9cbe79b326164965868e3ac0f426ad19
Source dataset
uspto-grants-2000_06
Patent number
US06071950

Reaction notes

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