Triethylamine → 3-(4-Benzylpiperazin-1-yl)propanethiol dihydrochloride

HRID 2290847

Reaction equation

HRID 2290847 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][Cl:23])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[ClH:23].[ClH:5].[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][SH:3])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 13731110Benzyl-4-(3-chloropropyl)piperazine dihydrochloride

Product 1

HCID 137311143-(4-Benzylpiperazin-1-yl)propanethiol dihydrochlorideYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

15 g of thiourea were added to a solution of 35 g of 1-benzyl-4-(3-chloropropyl)piperazine dihydrochloride, 20 g of triethylamine and 250 ml of reagent ethanol, and the mixture was refluxed for 8 hours. After the addition of a solution of 10 g of sodium hydroxide in 50 ml of water, the resulting mixture was refluxed for 4 additional hours. The ethanol was removed in vacuo, and water added to the residue which was extracted with methylene chloride, dried (sodium sulfate), and the salt was precipitated with ethereal hydrochloric acid to give 25.1 g (78% of theory) of 3-(4-benzylpiperazin-1-yl)propanethiol dihydrochloride as a white crystalline solid, M.p. 270°-273° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. temperaturethe resulting mixture was refluxed for 4 additional hours
  3. customThe ethanol was removed in vacuo, and water
  4. additionadded to the residue which
  5. extractionwas extracted with methylene chloride
  6. dry with materialdried (sodium sulfate)
  7. customthe salt was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-bd16d46356f54e52ade0e7d429a9301d
Source dataset
uspto-grants-1986_10
Patent number
US04618677

Linked notes

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