Ammonia → trans-1-(2-Aminoethyl)-4-[(phenylmethyl)amino]-3-piperidinol

HRID 654174Notes

Reaction equation

HRID 654174 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][N:4]([CH2:16][C:17]#[N:18])[CH2:3]1.N.[H][H]>[Ni].CO>[NH2:18][CH2:17][CH2:16][N:4]1[CH2:5][CH2:6][C@@H:7]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:2]([OH:1])[CH2:3]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14854945trans-3-Hydroxy-4-[(phenylmethyl)amino]-1-piperidineacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 67833560trans-1-(2-Aminoethyl)-4-[(phenylmethyl)amino]-3-piperidinolYield 91.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 12 parts of trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidineacetonitrile and 320 parts of methanol, saturated with ammonia was hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated to dry, yielding 11.2 parts (91.6%) of trans-1-(2-aminoethyl)-4-[(phenylmethyl)amino]-3-piperidinol as a residue (interm. 17).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customto dry

Sources & evidence

ORD record
ord-ae58485c610040b1aa0f126c234753b0
Source dataset
uspto-grants-1992_07
Patent number
US05130312

Reaction notes

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