Ethylamine → N-Ethyl-1-(1-phenylethyl)-3-pyrrolidinemethanamine

HRID 978591Notes

Reaction equation

HRID 978591 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH2:4]1.[CH2:16]([NH2:18])[CH3:17]>>[CH2:16]([NH:18][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH2:4]1)[CH3:17]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 13772860HCID 13772860, compound

Product 1

HCID 13772866N-Ethyl-1-(1-phenylethyl)-3-pyrrolidinemethanamineYield 98%

Procedure

A solution of 4.0 g (15.4 mmol) [3R - (R*,R*)]-3-(chloromethyl)-1-(1-phenylethyl)pyrrolidine in 60 ml 70% ethylamine was heated in a pressure bottle on the steam bath overnight. The mixture was cooled, filtered, and evaporated to a thick syrup which was treated with 50 ml 2N sodium hydroxide and extracted with 3×30 ml dichloromethane. The combined organic layer was dried (MgSO4) and evaporated to afford 3.49 g (98%) of the title compound as a syrup, [α]D +45.6° C. (C, 1.04, methanol).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customevaporated to a thick syrup which
  4. additionwas treated with 50 ml 2N sodium hydroxide
  5. extractionextracted with 3×30 ml dichloromethane
  6. dry with materialThe combined organic layer was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-ac936be646e944459e7c1b52b2466422
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

Loading…