Formaldehyde → HCID 22406718, compound

HRID 440510Notes

Reaction equation

HRID 440510 reaction equation
[C:1]([BH3-])#[N:2].[Na+].Br.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1([CH:17]2[C:26]3[C:21](=[CH:22][C:23]([F:29])=[C:24]([O:27][CH3:28])[CH:25]=3)[CH2:20][CH2:19]N2)[CH2:16][CH2:15]1.C=O>CO>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1([CH:17]2[C:26]3[C:21](=[CH:22][C:23]([F:29])=[C:24]([O:27][CH3:28])[CH:25]=3)[CH2:20][CH2:19][N:2]2[CH3:1])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22406832HCID 22406832, compound

Product 1

HCID 22406718HCID 22406718, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (2.8 g) was added at 5° C. to a mixture of 1-[1-(2,4-dichlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (10 g, prepared as described in Example RC4), methanol (100 ml) and 37-40% aqueous formaldehyde solution (7.2 ml). The mixture was warmed to ambient temperature and stirred for 1.5 hours. The solvent was removed in vacuo and the residue partitioned between water and dichloromethane. The organic phase was washed with concentrated ammonia solution, then water, and dried over magnesium sulphate. The solvent was removed in vacuo to yield 1-[1-(2,4-dichlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline as a gum which solidified on standing.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water and dichloromethane
  3. washThe organic phase was washed with concentrated ammonia solution
  4. dry with materialwater, and dried over magnesium sulphate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5a670d55ba0e4dd7bb5281ebd3851ac9
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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