Propyl mercaptan → HCID 69738094, compound

HRID 2121440Notes

Reaction equation

HRID 2121440 reaction equation
CC(C)([O-])C.[K+].C(S)CC.[CH:11]1([CH2:17][C@@H:18]([NH2:34])[CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32]C)[CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CN(C=O)C>[CH:11]1([CH2:17][C@@H:18]([NH2:34])[CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 7848Propyl mercaptan2×HCID 12052797HCID 12052797, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 69738094HCID 69738094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

Potassium t-butoxide is added portionwise to a stirred solution of propanethiol in dry DMF under an argon atmosphere. After 0.5 h, a solution of {(1R)-1-cyclohexylmethyl-2-[4-(2-methoxyphenyl)-piperazin-1-yl]-ethyl}-amine in dry DMF is added and the mixture is heated at 100° C. overnight. A further quantity of potassium t-butoxide and propanethiol is then added and the mixture heated at 100° C. for another 24 h. The cooled mixture is partitioned between water and ethyl acetate. The combined organic layers are washed with brine, dried and concentrated on a rotary evaporator to yield the desired product, which is purified by chromatography on alumina.

Workup

  1. temperaturethe mixture heated at 100° C. for another 24 h
  2. customThe cooled mixture is partitioned between water and ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. customdried
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f65886a670ee4a2cb0be83e56a165c68
Source dataset
uspto-grants-2004_02
Patent number
US06696450B2

Reaction notes

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