4-(2-Chloroethyl)phenol → 4-{2-[4-(3-Trifluoromethylphenyl)-piperidinyl]ethyl}phenol

HRID 487092Notes

Reaction equation

HRID 487092 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[OH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]Cl)=[CH:20][CH:19]=1>>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:25][CH2:24][C:21]3[CH:22]=[CH:23][C:18]([OH:17])=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 3167214-(2-Chloroethyl)phenolHCID 117363404-(3-(Trifluoromethyl)Phenyl)Piperidine

Product 1

HCID 148193254-{2-[4-(3-Trifluoromethylphenyl)-piperidinyl]ethyl}phenolYield 65%

Procedure

The procedure described in Example 1 was repeated except that 4-(3-trifluoromethylphenyl)piperidine (the product of Preparation L) and 2-(p-hydroxyphenyl)ethyl chloride were the respective starting materials employed, using the same molar porportions as before. In this particular case, the corresponding final product obtained 4-{2-[4-(3-trifluoromethylphenyl)-piperidinyl]ethyl}phenol (yield, 65%), which was also converted to the hydrochloride salt. The pure base product was characterized by means of nuclear magnetic resonance data: NMR (CDCl3) δ6.8-7.6 (m, 8H), 0.6-4.0 (m, 14H). The hydrochloride salt melted at 207°-210° C. and was further characterized by means of elemental analysis.

Sources & evidence

ORD record
ord-344767b1aaf34692bb31cbe0e4b2be51
Source dataset
uspto-grants-1994_03
Patent number
US05294619

Reaction notes

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