Water → HCID 21450992, compound

HRID 596191Notes

Reaction equation

HRID 596191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:17]=[C:16]([CH2:18][CH3:19])[S:15][C:10]=2[NH:11][CH2:12][CH2:13][N:14]=1.[N:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:17]=[C:16]([CH2:18][CH3:19])[S:15][C:10]=2[N:11]([C:26]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:27])[CH2:12][CH2:13][N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2420851-Piperidinecarbonyl chlorideHCID 135967971HCID 135967971, compound

Product 1

HCID 21450992HCID 21450992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 19.3 g of 5-o-chlorophenyl-7-ethyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine in 150 ml of tetrahydrofuran is added dropwise a solution of 10.8 g of 1-piperidinecarboxylic acid chloride in 30 ml of tetrahydrofuran with stirring. The whole solution is stirred under reflux for four and half hours. After cooling, the reaction mixture is transferred to water and extracted with ethyl acetate. After the extract is washed with water and dried over anhydrous magnesium sulfate, the solvent is evaporated under reduced pressure. The residue is treated with ethanolic hydrogen chloride to give 5-o-chlorophenyl-7-ethyl-1-piperidinocarbonyl-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepine hydrochloride as yellow crystals. This product, when recrystallized from a mixture of methanol and ethyl acetate, melts at 237°-238° C with decomposition.

Workup

  1. stirringThe whole solution is stirred
  2. temperatureunder reflux for four and half hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washAfter the extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. additionThe residue is treated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-b1cded5324314a3aa38a1e9a8657d4c9
Source dataset
uspto-grants-1977_03
Patent number
US04010184

Reaction notes

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