Ethanol → HCID 22449944, compound

HRID 2186802Notes

Reaction equation

HRID 2186802 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](N)([OH:26])[CH:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:28]([BH3-])#[N:29].[Na+].[OH-].[NH4+].[CH2:34](O)C>Cl.C=O.C(OC(=O)C)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:26])[CH:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH2:12][N:29]([CH3:28])[CH3:34])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22449933HCID 22449933, compound

Product 1

HCID 22449944HCID 22449944, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 712FormaldehydeSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.5 g of (+) threo 1-(p-nitrophenyl)-2-(4-benzylpiperidin-1-yl)-1-aminopropan-1-ol in 35 ml of ethanol and 9 ml of 2 M hydrochloric acid and 5 ml of formaldehyde 40% solution was added portionwise 1.1 g or sodiumcyanoborohydride. After stirring 1 h, the solution was diluted with ethylacetate and basified with a concentrated ammonium hydroxide solution. The organic phase was dried and the solvent removed, affording 3.8 g of (+) threo 1-(p-nitro-phenyl)-2- (4-benzylpiperidin-1-yl) -3-dimethylaminopropan-1-ol, m.p. 132-135° C.

Workup

  1. customThe organic phase was dried
  2. customthe solvent removed

Sources & evidence

ORD record
ord-848e6600c69c499c99c19476495ed181
Source dataset
uspto-grants-2002_06
Patent number
US06407122B1

Reaction notes

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