Formaldehyde → HCID 22406745, compound

HRID 440524Notes

Reaction equation

HRID 440524 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH2:14][CH2:13][NH:12]2)[CH2:10][CH2:9]1.C=O.[C:25]([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH2:14][CH2:13][N:12]2[CH3:25])[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22406797HCID 22406797, compound

Product 1

HCID 22406745HCID 22406745, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[1-(2-chlorophenyl)cyclopropyl]-7-methoxy-1,2,3,4-tetrahydroisoquinoline (2.5 g, prepared as described in Example RC10), 37-40% aqueous formaldehyde solution (2.9 ml), sodium cyanoborohydride (0.75 g) and acetonitrile (100 ml) was stirred for 15 minutes. Glacial acetic acid was added to neutralise the solution and stirring was continued for a further 45 minutes. The mixture was basified with aqueous sodium hydroxide solution, then extracted with ethyl acetate. The extracts yielded 1-[1-(2-chlorophenyl)cyclopropyl]-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. stirringstirring
  2. waitwas continued for a further 45 minutes
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-c97746190b544f85b38571dd5ea6fa05
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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