1-[2-(4-Iodophenoxy)ethyl]piperidine → HCID 21959160, compound

HRID 2214312Notes

Reaction equation

HRID 2214312 reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:26]=[CH:25][C:10]2[C:11]3[CH:20]([OH:21])[O:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=3[CH2:22][CH2:23][O:24][C:9]=2[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].I[C:30]1[CH:44]=[CH:43][C:33]([O:34][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:32][CH:31]=1>>[C:1]([Si:5]([CH3:27])([CH3:28])[O:6][C:7]1[CH:26]=[CH:25][C:10]2[C:11]([CH:20]([OH:21])[C:30]3[CH:31]=[CH:32][C:33]([O:34][CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)=[CH:43][CH:44]=3)=[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[OH:19])[CH2:22][CH2:23][O:24][C:9]=2[CH:8]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 154806551-[2-(4-Iodophenoxy)ethyl]piperidineHCID 21051989HCID 21051989, compound

Product 1

HCID 21959160HCID 21959160, compound

Procedure

Following the procedure described in Examples 76, 2-(tert-Butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-ol, the compound prepared as in Example 105 above, was reacted with 1-[2-(4-Iodo-phenoxy)-ethyl]-piperidine to yield 2-(8-(tert-Butyl-dimethyl-silyloxy)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-2,3-dihydro-benzo[b]oxepin-4-yl)-phenol as a crude oil. The crude 2-(8-(tert-Butyl-dimethyl-silyloxy)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-2,3-dihydro-benzo[b]oxepin-4-yl)-phenol was then further treated with HCl (12N, 4 eq., 0.67 mL) in toluene (100 mL) to generate yield 1-(2-{4-[2-(tert-Butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]-phenoxy}-ethyl)-piperidine as a crude oil. The crude 1-(2-{4-[2-(tert-Butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]-phenoxy}-ethyl)-piperidine was then further treated with HF•Pyridine (70% HF, 30% Pyridine, 0.5 mL) in CH3CN (20 mL) at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate:THF (1:1) and then washed with 5% NaHCO3 and brine. The reaction mixture was dried, concentrated and purified by flash chromatograph eluted with 5% MeOH in DCM to yield the title compound as a slightly yellow solid.

Workup

  1. customthe compound prepared as in Example 105 above,

Sources & evidence

ORD record
ord-3f4643d259ce43b4ad5186e6bdd42586
Source dataset
uspto-grants-2006_09
Patent number
US07105679B2

Reaction notes

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