Thionyl Chloride → HCID 13772860, compound

HRID 868136Notes

Reaction equation

HRID 868136 reaction equation
[C:1]1([CH:7]([N:9]2[CH2:13][CH2:12][CH:11]([CH2:14]O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>ClCCCl>[Cl:18][CH2:14][CH:11]1[CH2:12][CH2:13][N:9]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH2:10]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13772857HCID 13772857, compound

Product 1

HCID 13772860HCID 13772860, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 0.50 g (2.44 mmol) [3R-(R*,R*)]-1-(1-phenylethyl)-3-pyrrolidinemethanol in 5 ml 1,2-dichloroethane was treated with 2 ml thionyl chloride, refluxed two hours, evaporated, and crystallized by trituration with ether to afford 0.64 g (100%) of the title compound as the hydrochloride mp 140°-146 ° C., [α]D +27.8° C. (c, 1.07, methanol).

Workup

  1. temperaturerefluxed two hours
  2. customevaporated
  3. customcrystallized by trituration with ether

Sources & evidence

ORD record
ord-b0d13626d303410c82b3878db19c4348
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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