Sodium cyanoborohydride → HCID 20556403, compound

HRID 263067Notes

Reaction equation

HRID 263067 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([N:6]([CH:13]1[CH2:19][CH2:18][CH2:17][CH:16]([Cl:20])[CH2:15][C:14]1=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].C([BH3-])#N.[Na+].[CH3:26][NH:27][CH3:28].Cl.CNC>CO>[Cl:1][CH2:2][CH2:3][C:4]([N:6]([CH:13]1[CH2:19][CH2:18][CH2:17][CH:16]([Cl:20])[CH2:15][CH:14]1[N:27]([CH3:28])[CH3:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 53642397HCID 53642397, compoundHCID 86736553HCID 86736553, compound

Product 1

HCID 20556403HCID 20556403, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 3,4-dichloro-N-[2-oxocycloheptyl]propionanilide from Part C above is treated with sodium cyanoborohydride and dimethylamine-dimethylamine hydrochloride in methanol in the presence of 3A molecular sieves; the resulting mixture is worked up under basic pH conditions and the organic residue is chromatographed (column) on silica gel to isolate the cis isomer of 3,4-dichloro-N-[2-(dimethylamino)cycloheptyl]propionanilide.

Workup

  1. customthe organic residue is chromatographed (column) on silica gel

Sources & evidence

ORD record
ord-5b107de3325b454cb82e871bb21f5b60
Source dataset
uspto-grants-1979_05
Patent number
US04156014

Reaction notes

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