Thionyl Chloride → HCID 66853164, compound

HRID 1406432Notes

Reaction equation

HRID 1406432 reaction equation
S(Cl)([Cl:3])=O.[N:5]1([CH2:10][C:11]2([CH2:14]O)[CH2:13][CH2:12]2)[CH2:9][CH2:8][CH2:7][CH2:6]1>C1(C)C=CC=CC=1>[ClH:3].[Cl:3][CH2:14][C:11]1([CH2:10][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66854227(1-(pyrrolidin-1-ylmethyl)cyclopropyl)methanol

Product 1

HCID 66853164HCID 66853164, compoundYield 111.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Thionyl chloride (1 mL, 13.7 mmol) was added to a solution of (1-pyrrolidin-1-ylmethyl-cyclopropyl)-methanol (1.45 g, 9.3 mmol) in toluene (20 mL) to give a pale brown suspension. The suspension was heated, 110° C., for ˜3 hrs. to give a dark brown suspension. The resulting suspension was allowed to cool and concentrated to a brown solid. Tritruation with diethyl ether (40 mL) gave the desired intermediate, 1-(1-chloromethyl-cyclopropylmethyl)-pyrrolidine hydrochloride as a brown powder 1.6 g, 82%.

Workup

  1. customto give a pale brown suspension
  2. customto give a dark brown suspension
  3. temperatureto cool
  4. concentrationconcentrated to a brown solid

Sources & evidence

ORD record
ord-550ee2b99c3942b4987e4142eedaf722
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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