3,4-Dimethoxyphenethyl alcohol → N-{4-[2-(3,4-Dimethoxyphenyl)ethoxy]-1-naphthyl}-3-fluoro-5-piperidin-1-ylbenzamide

HRID 1641233Notes

Reaction equation

HRID 1641233 reaction equation
C(O[C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[CH:10][CH:9]=1)(C)(C)C.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:29]=1)C(O)=O.[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH2:46][CH2:47]O)[CH:41]=[CH:42][C:43]=1[O:44][CH3:45]>>[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH2:46][CH2:47][O:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH:7][C:6](=[O:19])[C:23]3[CH:27]=[C:28]([N:30]4[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)[CH:29]=[C:21]([F:20])[CH:22]=3)=[CH:9][CH:10]=2)[CH:41]=[CH:42][C:43]=1[O:44][CH3:45]

Participants

4

Reactant 3

HCID 819113,4-Dimethoxyphenethyl alcoholHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Product 1

HCID 59553461N-{4-[2-(3,4-Dimethoxyphenyl)ethoxy]-1-naphthyl}-3-fluoro-5-piperidin-1-ylbenzamide

Procedure

Compound is prepared from tert-butyl(4-hydroxy-1-naphthyl)carbamate, 3-fluoro-5-piperidin-1-yl-benzoic acid and 2-(3,4-Dimethoxy-phenyl)-ethanol according to conditions described in general procedure D. A deep pink solid is produced (42 mg). Mp: 158-160° C.; 1H NMR (300 MHz, CDCl3) δ 1.60-1.68(m, 6H), 3.00(d, J=6.3 Hz, 1H), 3.18-3.27(m, 5H), 3.85-3.87(m, 6H), 4.35(d, J=6.6 Hz, 1H), 4.48(d, J=7.2 Hz, 1H), 6.71-6.91(m, 4H), 6.98(d, J=7.8 Hz, 1H), 7.08(d, J=8.4 Hz, 1H), 7.30-7.34(m, 1H), 7.46-7.56(m, 2H), 7.69(d, J =7.8 Hz, 1H), 7.82(d, J=7.8 Hz, 1H), 7.94(s, 1H), 8.33(d, J=9.0 Hz, 1H); MS 529 (M+1).

Workup

  1. customA deep pink solid is produced (42 mg)

Sources & evidence

ORD record
ord-980a578ec55b494f9f4eaaf58e925a53
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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