Dichloromethane → 2-Acetyl-5-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-isoquinoline

HRID 597207Notes

Reaction equation

HRID 597207 reaction equation
Cl.[CH2:2]([O:9][C:10]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][NH:14][CH2:15]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:22]([O-])(=[O:24])[CH3:23].[Na+].C(OC(=O)C)(=O)C.C(Cl)Cl>O>[C:22]([N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:10]=2[O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:15]1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 21447025HCID 21447025, compound

Product 1

HCID 214470072-Acetyl-5-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-isoquinolineYield 79.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 122.3 g of 5-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-isoquinoline-hydrochloride, 36.1 g of sodium acetate, 81.7 g of acetic anhydride, and 500 ml of methylene chloride is stirred for 1 hour at the boiling point. After cooling, the mixture is combined with 500 ml of water and the organic phase is separated and evaporated to dryness under reduced pressure. 99.5 g of 2-acetyl-5-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-isoquinoline are obtained. m.p. = 94° - 95° C. (ethyl acetate - diisopropyl ether).

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is separated
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-955f010b617943459fe35ffb7051e9cf
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

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