Ethanol → 1-[4-(Pyrrolidin-1-ylmethyl)phenyl]cyclopropanecarboxylic acid

HRID 557903Notes

Reaction equation

HRID 557903 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]#N)[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([OH:20])C.[OH-:21].[Na+]>O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]([OH:20])=[O:21])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 666623631-[4-(Pyrrolidin-1-ylmethyl)phenyl]cyclopropanecarbonitrile

Product 1

HCID 666618531-[4-(Pyrrolidin-1-ylmethyl)phenyl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclopropanecarbonitrile (100 mg, 0.0004 mol) in ethanol (5 mL, 0.08 mol) and 50% NaOH (aq. 4 ml) and water (2 ml) was stirred at 100 celsius overnight. The mixture was then carefully adjusted to be slightly acidic (pH=6) and the precipitate formed was filtered and dried to afford the product. LC-MS: 246.1 (M+H)+

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. customdried
  4. customto afford the product

Sources & evidence

ORD record
ord-5cf2b9ab5a4b44c994eab4b893b70651
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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