HCID 67919251, compound → 1-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amine

HRID 1885719Notes

Reaction equation

HRID 1885719 reaction equation
[C:1]1([NH:7][C:8]2([CH:21](C3SC=CC=3)[O:22][CH3:23])[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18]C=CC=3)[CH:10](C)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C>[C:1]1([NH:7][C:8]2([CH2:21][O:22][CH3:23])[CH2:9][CH2:10][N:11]([CH2:14][C:19]3[CH:18]=[CH:3][CH:2]=[CH:1][CH:6]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 67919251HCID 67919251, compound

Product 1

HCID 30477241-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amineYield 110.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Raney nickel (38 g, wet, W-2, washed with ethanol, then ethyl acetate) was added to a solution of 4-phenylamino-4-(1-thiophenyl-1-methoxymethyl)-N-phenyl-methyl piperidine (3.10 g, 7.4 mmole) in ethyl acetate (100 ml). The resulting mixture was stirred at room temperature for 1 hour, filtered through a sintered glass funnel and the filtrate concentrated under vacuum. The resulting residue was chromatographed (silica gel; ethyl acetate) to yield the product, 4-phenylamino-4-methoxymethyl-N-phenylmethyl piperidine, (1.27 g, 4.1 mmole) in 55% yield as a colorless oil.

Workup

  1. washRaney nickel (38 g, wet, W-2, washed with ethanol
  2. filtrationfiltered through a sintered glass funnel
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe resulting residue was chromatographed (silica gel; ethyl acetate)

Sources & evidence

ORD record
ord-9c8da7144a7c4a8a8c578ed8f1d1cd4a
Source dataset
uspto-grants-1992_09
Patent number
US05145967

Reaction notes

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