3-(4-Fluorobenzoyl)propyl chloride → alpha-Phenyl-4-(5-fluoro-1-naphthalenyloxy)-1-piperidinepropanol

HRID 325966Notes

Reaction equation

HRID 325966 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.CC1C2C(=CC=CC=2)C=CC=1ON1CCCCC1.Br[CH2:38][CH2:39][CH:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:41].ClCCCC(C1C=CC(F)=CC=1)=O>>[C:42]1([CH:40]([OH:41])[CH2:39][CH2:38][N:16]2[CH2:15][CH2:14][CH:13]([O:12][C:7]3[C:8]4[C:3](=[C:2]([F:1])[CH:11]=[CH:10][CH:9]=4)[CH:4]=[CH:5][CH:6]=3)[CH2:18][CH2:17]2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 4

HCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 135612983-Bromo-1-phenylpropan-1-OLHCID 204631974-(5-Fluoro-1-naphthalenyloxy)piperidineHCID 20463207(1-Methyl-2-naphthalenyloxy)piperidine

Product 1

HCID 20463211alpha-Phenyl-4-(5-fluoro-1-naphthalenyloxy)-1-piperidinepropanol

Procedure

When in the procedure of Example 18, 4-(5-fluoro-1-naphthalenyloxy)piperidine is substituted for (1-methyl-2-naphthalenyloxy)piperidine and 3-bromo-1-phenylpropanol substituted for 4-chloro-1-(4-fluorophenyl)-1-butanone, α-phenyl-4-(5-fluoro-1-naphthalenyloxy)-1-piperidinepropanol is obtained.

Sources & evidence

ORD record
ord-91c84d6ddcfe48a5ac999ccd7355912f
Source dataset
uspto-grants-1984_04
Patent number
US04443462

Reaction notes

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