Thionyl Chloride → 2-(N-Cyclohexyl-N-methyl-amino)-1-chloroethane

HRID 979507Notes

Reaction equation

HRID 979507 reaction equation
[CH:1]1([N:7]([CH3:11])[CH2:8][CH2:9]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:14])=O>C(OCC)C>[CH:1]1([N:7]([CH2:8][CH2:9][Cl:14])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2775822-(Cyclohexylmethylamino)ethanol

Product 1

HCID 38492302-(N-Cyclohexyl-N-methyl-amino)-1-chloroethane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

N-Cyclohexyl-N-methyl-2-aminoethanol (25 g) is added dropwise to thionyl chloride (120 cc) and then the mixture is heated for 24 hours at 70° C. After the excess thionyl chloride has been distilled off, the orange oil obtained is stirred into ethyl ether (200 cc) to give a white solid, which is separated off by filtrattion and then washed with ether. 2-(N-Cyclohexyl-N-methyl-amino)-1-chloroethane (30 g) is obtained in the form of a white solid melting at 154° C.

Workup

  1. distillationAfter the excess thionyl chloride has been distilled off
  2. customthe orange oil obtained
  3. customto give a white solid, which
  4. customis separated off by filtrattion
  5. washwashed with ether

Sources & evidence

ORD record
ord-409157e92237484db0194f7396b5ea70
Source dataset
uspto-grants-1987_05
Patent number
US04668669

Reaction notes

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