4-Benzhydrylpiperidine → 4-Diphenylmethyl-1-iminomethylpiperidine hydrochloride hydrate

HRID 1413947Notes

Reaction equation

HRID 1413947 reaction equation
[ClH:1].[CH:2](=[NH:6])[O:3]CC.[C:7]1([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[OH2:3].[ClH:1].[C:7]1([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]2[CH2:15][CH2:16][N:17]([CH:2]=[NH:6])[CH2:18][CH2:19]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 882784-BenzhydrylpiperidineHCID 12578842Ethyl formimidate hydrochloride

Product 1

HCID 202912354-Diphenylmethyl-1-iminomethylpiperidine hydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 27.39 g (0.25 mole) of ethyl formimidate hydrochloride [prepared by the method of Ohme, et al., Angew. Chem. Intl. Ed., 6, 566(1967)] and 52.71 g (0.20 mole) of diphenyl-4-piperidylmethane in 80 ml of freshly-opened absolute ethanol was stirred magnetically under a calcium chloride tube overnight. The suspension was filtered and diethylether was added to the filtrate. The filtrate was stripped to dryness and the resulting oil was crystallized from isopropanol. The solid was then suspended in boiling ethyl acetate to obtain a higher melting form. Two recrystallizations from ethanol-ether yielded pure 4-diphenylmethyl-1-iminomethylpiperidine hydrochloride hydrate; m.p. 220°-221° C.

Workup

  1. customprepared by the method of Ohme, et al., Angew
  2. filtrationThe suspension was filtered
  3. additiondiethylether was added to the filtrate
  4. customthe resulting oil was crystallized from isopropanol
  5. customto obtain
  6. customTwo recrystallizations from ethanol-ether yielded pure 4-diphenylmethyl-1-iminomethylpiperidine hydrochloride hydrate

Sources & evidence

ORD record
ord-080906e86704466ab5765c768ea24b35
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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