Thionyl Chloride → 1-Benzyl-2-(chloromethyl)pyrrolidinium chloride

HRID 1669448Notes

Reaction equation

HRID 1669448 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[Cl-:17].[CH2:1]([NH+:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 562951(1-Benzylpyrrolidin-2-yl)methanol

Product 1

HCID 866279031-Benzyl-2-(chloromethyl)pyrrolidinium chlorideYield 100%

Conditions

Temperature
35 °C

Procedure

(1-benzylpyrrolidin-2-yl)methanol was slowly added to thionyl chloride (45 eq) and the resulting mixture was stirred for 15 h at 35° C. All the volatiles were removed in vacuo. The yellow oil residue was treated with Et2O and re-evaporated to drive off excess thionyl chloride. The crude material was then dried at the high vacuum pump for 2 h to afford the product (100%). 1H NMR (400 MHz, CDCl3) 1.85-2.01 (m, 1H), 2.15-2.32 (m, 3H), 2.85-3.05 (m, 1H), 3.43-3.54 (m, 1H), 3.65-3.79 (m, 1H), 3.92-4.02 (m, 2H), 4.20-4.22 (m, 1H), 4.41-4.43 (m, 1H), 7.44-7.62 (m, 5H).

Workup

  1. customAll the volatiles were removed in vacuo
  2. additionThe yellow oil residue was treated with Et2O
  3. customre-evaporated
  4. dry with materialThe crude material was then dried at the high vacuum pump for 2 h

Sources & evidence

ORD record
ord-5a60869f6f724084a56a6499b9544ce5
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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