Hydrochloric Acid → 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 27166Notes

Reaction equation

HRID 27166 reaction equation
[ClH:1].P([O-])([O-])([O-])=O.[CH2:7]([O:14][C:15]([N:17]([CH2:25][C:26]1[C:35]2[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=2)[CH2:29][CH2:28][N:27]=1)[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[BH4-].[Na+]>C(O)C>[ClH:1].[CH2:7]([O:14][C:15]([N:17]([CH2:25][CH:26]1[C:35]2[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=2)[CH2:29][CH2:28][NH:27]1)[C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1061PhosphateHCID 4311764Sodium borohydrideHCID 204605121-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline

Product 1

HCID 204605451-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of hydrochloride and phosphate of 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline (4.6 g) was dissolved in 99% ethanol (45 ml). To the solution was added sodium borohydride (0.8 g) with stirring under ice cooling, and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated to dryness under reduced pressure and to the residue was added water. The mixture was saturated with sodium chloride and extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The oil obtained was treated with ethanol containing hydrochloric acid to give 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.3 g), mp 189° to 190° C.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure and to the residue
  3. additionwas added water
  4. extractionextracted with ethyl acetate
  5. customThe extract was dried
  6. distillationthe solvent was distilled off
  7. customThe oil obtained

Sources & evidence

ORD record
ord-cac5ff9e0025474e81b470f2dc9d1cd2
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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