N-[3-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-2-pyridinyl]-2,2-dimethylpropanamide → HCID 18321331, compound

HRID 1699231Notes

Reaction equation

HRID 1699231 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]3[C:17]([NH:22]C(=O)C(C)(C)C)=[N:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl>[NH2:22][C:17]1[C:16]([CH2:15][NH:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:13][CH2:12]2)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

3

Reactant 1

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

Product 1

HCID 18321331HCID 18321331, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 6.0 g (0.0158 mol) of N-[3-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-2-pyridinyl]-2,2-dimethylpropanamide and 100 ml of conc. hydrochloric acid was refluxed for 3 hours. The mixture was evaporated down in vacuo, the residue remaining was dissolved in a little water and made alkaline by the addition of solid potassium carbonate. It was extracted thoroughly with ethyl acetate, the combined extracts were dried over sodium sulphate and evaporated down in vacuo. The residue was thoroughly triturated with diisopropylether and yielded 4.2 g (89.7% of theory) of colourless crystals of melting point 114° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe mixture was evaporated down in vacuo
  3. dissolutionthe residue remaining was dissolved in a little water
  4. additionby the addition of solid potassium carbonate
  5. extractionIt was extracted thoroughly with ethyl acetate
  6. dry with materialthe combined extracts were dried over sodium sulphate
  7. customevaporated down in vacuo
  8. customThe residue was thoroughly triturated with diisopropylether
  9. customyielded 4.2 g (89.7% of theory) of colourless crystals of melting point 114° C.

Sources & evidence

ORD record
ord-a70b61686fdf43a8aad240c08a1d3b64
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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