Dimethylamine → N,N-Dimethyl-2,2-diphenylcyclopropanemethanamine

HRID 2420275Notes

Reaction equation

HRID 2420275 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]1([C:10]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12][CH:11]2[CH2:13]Cl)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C>C(O)C>[CH3:1][N:2]([CH2:13][CH:11]1[CH2:12][C:10]1([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:3]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 203114721,1'-[2-(Chloromethyl)cyclopropane-1,1-diyl]dibenzene

Product 1

HCID 522110N,N-Dimethyl-2,2-diphenylcyclopropanemethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 40% aqueous dimethylamine (10 ml) in ethanol (10 ml) was added a solution of 2,2-diphenylcyclopropylmethyl chloride (0.50 g) in ethanol (10 ml) and triethylamine (1.0 g) at room temperature, and stirring was carried out at 35°-40° C for 32 hours. The reaction mixture was evaporated and poured into a 10% aqueous sodium hydroxide solution. The etheral extract was dried and chromatographed to afford N,N-dimethyl-2,2-diphenylcyclopropylmethylamine as an oily substance. M.P. 231°-233° C (hydrochloride).

Workup

  1. customThe reaction mixture was evaporated
  2. additionpoured into a 10% aqueous sodium hydroxide solution
  3. extractionThe etheral extract
  4. customwas dried
  5. customchromatographed

Sources & evidence

ORD record
ord-950159e37e654de08165c72d001fd698
Source dataset
uspto-grants-1978_08
Patent number
US04110376

Reaction notes

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