1-Benzyl-4-piperidylamine → N-[3-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-2-pyridinyl]-2,2-dimethylpropanamide

HRID 1699230Notes

Reaction equation

HRID 1699230 reaction equation
[CH:1]([C:3]1[C:4]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][CH:6]=[CH:7][CH:8]=1)=O.[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1.[BH4-].[Na+]>CO>[C:24]1([CH2:23][N:20]2[CH2:21][CH2:22][CH:17]([NH:16][CH2:1][C:3]3[C:4]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][CH:6]=[CH:7][CH:8]=3)[CH2:18][CH2:19]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 4158521-Benzyl-4-piperidylamineHCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamideHCID 4311764Sodium borohydride

Product 1

HCID 18321280N-[3-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-2-pyridinyl]-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8.2 g (0.0398 mol) of N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide and 7.6 g (0.04 mol) of 4-amino-1-(phenylmethyl)piperidine in 80 ml of methanol was combined in batches with a total of 1.7 g (0.045 mol) of sodium borohydride and refluxed for a total of 24 hours. The solvent was removed in vacuo, the residue was distributed between water and ethyl acetate. The organic phase was dried over sodium sulphate and freed from solvent. The residue was triturated with diisopropylether and suction filtered. 6.0 g (39.6% of theory) of colourless crystals of melting point 138° C. were obtained.

Workup

  1. temperaturerefluxed for a total of 24 hours
  2. customThe solvent was removed in vacuo
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customThe residue was triturated with diisopropylether and suction
  5. filtrationfiltered
  6. custom6.0 g (39.6% of theory) of colourless crystals of melting point 138° C. were obtained

Sources & evidence

ORD record
ord-2d1fce0e207643bd887f56097341265a
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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