Water → HCID 19991510, compound

HRID 345860Notes

Reaction equation

HRID 345860 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:12](=[O:15])[CH2:13][Cl:14].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>C(Cl)Cl>[ClH:14].[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:12](=[O:15])[CH2:13][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 14721052HCID 14721052, compound

Product 1

HCID 19991510HCID 19991510, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-1-phenyl-2-(2-chloroacetyl)-1,2,3,4-tetrahydroisoquinoline (1.0 g) in methylene chloride (10 ml) was added piperidine (0.82 ml) under ice-cooling, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium bicarbonate, sodium chloride aqueous solution and dried over magnesium sulfate, evaporated in vacuo. The residue was dissolved in ethanol (5 ml) and to the solution was added 6M ethanol solution of hydrogen chloride (1 ml). The mixture was evaporated in vacuo and the residue was recrystallized from isopropyl alcohol and diisopropyl ether. The crystal was washed with diethyl ether and dried in vacuo to give 1-methyl-1-phenyl-2-(2-piperidino-acetyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.4 g).

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate, sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in ethanol (5 ml) and to the solution
  7. additionwas added 6M ethanol solution of hydrogen chloride (1 ml)
  8. customThe mixture was evaporated in vacuo
  9. customthe residue was recrystallized from isopropyl alcohol and diisopropyl ether
  10. washThe crystal was washed with diethyl ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-a227967e0ee54575bfc7a1f4efb738dd
Source dataset
uspto-grants-1991_10
Patent number
US05059608

Reaction notes

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