Ammonia → 1-Benzyl-piperidine-4-carboxamidine dihydrochloride

HRID 419711Notes

Reaction equation

HRID 419711 reaction equation
[ClH:1].CO[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[NH:5].[NH3:19]>CO>[ClH:1].[ClH:1].[CH2:12]([N:9]1[CH2:10][CH2:11][CH:6]([C:4]([NH2:19])=[NH:5])[CH2:7][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 666500581-Benzyl-piperidine-4-carboximidic acid methyl ester hydrochloride

Product 1

HCID 666498531-Benzyl-piperidine-4-carboxamidine dihydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1-benzyl-piperidine-4-carboximidic acid methyl ester hydrochloride (17.47 g 1.00 equiv; 65 mmoles) in 2M ammonia in methanol (˜350 mL). Saturate with ammonia gas for 15 min. Stir for 18 hours and evaporate. Co-evaporate with dry methanol. Dry under high vacuum to give 18.29 g (63.03 mmol, 97%) of 1-benzyl-piperidine-4-carboxamidine dihydrochloride as a light yellow solid.

Workup

  1. concentrationSaturate with ammonia gas for 15 min
  2. customevaporate
  3. customCo-evaporate with dry methanol
  4. customDry under high vacuum

Sources & evidence

ORD record
ord-e0d400d3d8724e68bc1210edb7eb3270
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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