Sodium Hydroxide → N,N-Dimethyl-2,2-diphenylcyclopropanemethanamine

HRID 2420274Notes

Reaction equation

HRID 2420274 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:26])[C:9]([CH:11]1[CH2:13][C:12]1([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[OH-].[Na+]>CCOCC>[CH3:26][N:8]([CH2:9][CH:11]1[CH2:13][C:12]1([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53646980HCID 53646980, compound

Product 1

HCID 522110N,N-Dimethyl-2,2-diphenylcyclopropanemethanamineYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of lithium aluminum hydride (0.30 g) in ether (10 ml) was added a solution of 2,2-diphenylcyclopropanecarboxylic acid N,N-dimethylamide (0.813 g) in ether (15 ml) under ice-cooling, and the resulting mixture was stirred under reflux for 2 hours. The reaction mixture was cooled, admixed with a 10% aqueous solution of sodium hydroxide (20 ml) and extracted with ether. The ether extract was dried over anhydrous magnesium sulfate and evaporated to afford N,N-dimethyl-2,2-diphenylcyclopropylmethylamine (0.701 g) as an oily substance. M.P. 231°-233° C (hydrochloride).

Workup

  1. temperaturecooling
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8c84b51a1ce84642b7a08bf903d7c96c
Source dataset
uspto-grants-1978_08
Patent number
US04110376

Reaction notes

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