Potassium Carbonate → 4-[2-(Diphenylmethoxy)ethyl]-1-[(4-iodophenyl)methyl]piperidine

HRID 890360Notes

Reaction equation

HRID 890360 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+].C([O-])(=O)C([O-])=O>CCO>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:28][C:27]3[CH:30]=[CH:31][C:24]([I:23])=[CH:25][CH:26]=3)[CH2:13][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 71081OxalateHCID 9542584-Iodobenzyl bromideHCID 107326614-(2-(Diphenylmethoxy)ethyl]piperidine

Product 1

HCID 99143274-[2-(Diphenylmethoxy)ethyl]-1-[(4-iodophenyl)methyl]piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[2-(diphenylmethoxy)ethyl]piperidine (0.23 g, 0.77 mmol) was reacted with 4-iodo benzyl bromide (0.76 g, 2.5 mmol) and K2CO3 (1.00 g, 7 mmol) in EtOH (10 mL) to give a thick oil, 0.17 g (%). 1H NMR (300 MHz, CDCl3): 1.21-1.63 (7H, m), 1.87-1.93 (t, J=11 Hz, 2H, N(CH2)—), 2.79-2.83 (bd, J=12 Hz, 2H, N(CH2)—), 3.41-3.49 (4H, m), 5.31 (s, 1H, Ph2CHO—), 7.05-7.63 (14H, m, ArH). Free base was converted into its oxalate sale, m.p.=160-161 ° C. Anal. C27H30INO. (COOH)2.

Workup

  1. customto give a thick oil, 0.17 g (%)

Sources & evidence

ORD record
ord-9961ff9fac9b4e07a532fc1da20b651a
Source dataset
uspto-grants-2006_02
Patent number
US06995268B2

Reaction notes

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