Sodium Bicarbonate → HCID 23294282, compound

HRID 1955207Notes

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.[OH: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.[Na+]>>[ClH:1].[OH: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 516892Sodium Bicarbonate

HCID 128339324-(2-Bromoethoxy)phenol

HCID 23294418HCID 23294418, compound

Product 1

HCID 23294282HCID 23294282, compound

Procedure

The title compound was prepared from 4-((2-naphthyl)methyl)piperidine hydrochloride (150 mg, 573 μmol), 2-(4-hydroxyphenoxy)ethyl bromide (130 mg, 602 μmol) and NaHCO3 (97 mg, 1.17 mmol) as a pale yellow solid (182 mg): mp 221-222° C.; 1H NMR (CD3OD) 1.53-1.72 (m, 2H), 1.87-2.12 (m, 3H), 2.81 (d, J=6.9 Hz, 2H), 2.92-3.18 (m, 2H), 3.43-3.70 (m, 4H), 4.25 (t, J=4.8 Hz, 2H), 6.73 (d, J=9.3 Hz, 2H), 6.85 (d, J=9.3 Hz, 2H), 7.32-7.49 (m, 3H), 7.66 (s, 1H), 7.76-7.85 (m, 3H); Anal. Calcd for C24H28ClNO2 ·0.4H2O: C, 71.15; H, 7.16; N, 3.46. Found: C, 71.17; H. 6.80; N, 3.11.

Sources & evidence

ORD record: ord-5fb9d334b39048429771759d59cd2827
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124323

Reaction notes

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