Diazomethane → 4-Piperidinamine, 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-

HRID 37370Notes

Reaction equation

HRID 37370 reaction equation
[C:1]1([NH:7][C:8]2([CH2:22][OH:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:26])=[N-]>CCOCC>[CH3:26][O:23][CH2:22][C:8]1([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 122982044-Piperidinemethanol, 4-(phenylamino)-1-(2-phenylethyl)-

Product 1

HCID 122982104-Piperidinamine, 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 4-(N-phenylamino)-1-(2-phenylethyl)-4-piperidinylmethanol (0.100 g) and silica (0.5 g) in ether (5 ml) at room temperature was added an excess of ethereal diazomethane, and the mixture stirred at room temperature until no more colour remained. The reaction mixture was filtered and the filtrate concentrated to give an oil. Purification on silica gel using chloroform-methanol 38:1 as eluant gave the title compound (0.052 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customto give an oil
  4. customPurification on silica gel

Sources & evidence

ORD record
ord-1e2b3efd18e84c18ae00edd6798bb2ae
Source dataset
uspto-grants-1995_05
Patent number
US05420280

Reaction notes

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