Phenylacetyl chloride → 2-Phenylacetyldecahydroisoquinoline

HRID 1654661Notes

Reaction equation

HRID 1654661 reaction equation
[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][NH:2]1.[OH-].[Na+].[C:13]1([CH2:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:13]1([CH2:19][C:20]([CH:1]2[CH:10]3[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]3)[CH2:4][CH2:3][NH:2]2)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 97812Decahydroisoquinoline

Product 1

HCID 700728582-Phenylacetyldecahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 5.0 g of decahydroisoquinoline (mixture of cis and trans isomers), 20 mL of methylene chloride and 50 mL of 15% aqueous sodium hydroxide solution was added at 10°-15° a solution of 7 mL of phenylacetyl chloride in 20 mL of methylene chloride. Removal of the solvent from the dried organic layer and crystallizaiton of the residue from hexanes gave 3.12 g of 2-phenylacetyldecahydroisoquinoline.

Workup

  1. customRemoval of the solvent from the dried organic layer and crystallizaiton of the residue from hexanes

Sources & evidence

ORD record
ord-9e45302f58a44d328f6ab0fb04c8158f
Source dataset
uspto-grants-1995_04
Patent number
US05409929

Reaction notes

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