Potassium Carbonate → HCID 23294509, compound

HRID 1955208Notes

Reaction equation

[ClH:1].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[F:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]Br)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>>[ClH:1].[F:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][N:16]2[CH2:17][CH2:18][CH:13]([CH2:12][C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:2]=3)[CH2:14][CH2:15]2)=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 20641711-(2-Bromoethoxy)-4-fluorobenzene

HCID 23294418HCID 23294418, compound

Product 1

HCID 23294509HCID 23294509, compound

Procedure

The title compound was prepared from 4-((2-naphthyl)methyl)piperidine hydrochloride (150 mg, 573 μmol), 2-(4-fluorophenoxy)ethyl bromide (132 mg, 602 μmol) and K2CO3 (162 mg, 1.17 mmol) as a colorless solid (126 mg): mp 170-172° C.; 1H NMR (CDCl3) 1.60-1.92 (m, 3H), 2.02-2.41 (m, 2H), 2.65-2.90 (m, 4H), 3.45-3.55 (m, 2H), 3.60-3.71 (m, 2H), 4.51 (t, J=4.2 Hz, 2H), 6.77-7.01 (m, 4H), 7.25 (d, J=6.0 Hz, 1H), 7.40-7.51 (m, 2H), 7.57 (s, 1H), 7.72-7.84 (m, 3H) 12.64 (bs, 1H). Anal. Calcd for C24H27ClFNO: C, 72.08; H, 6.80; N, 3.50. Found: C, 71.73; H, 6.64; N, 3.34.

Sources & evidence

ORD record: ord-dd77e1270d3940089f031bd1de98c370
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124323

Reaction notes

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