3-(4-Fluorobenzoyl)propyl chloride → 6-[4-(4-Trifluoromethyl-2-naphthalenyloxy)-1-piperidyl]-1-(4-methoxyphenyl)-1-hexanone

HRID 325965Notes

Reaction equation

HRID 325965 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([O:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:4]=1.CC1C2C(=CC=CC=2)C=CC=1OC1CCNCC1.Br[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=1)=[O:47].ClCCCC(C1C=CC(F)=CC=1)=O>>[F:21][C:2]([F:1])([F:20])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([C:48]3[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=3)=[O:47])[CH2:16][CH2:15]2)[CH:4]=1

Participants

5

Reactant 4

HCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 106131051-Hexanone, 6-bromo-1-(4-methoxyphenyl)-HCID 204632094-(1-Methyl-2-naphthalenyloxy)piperidineHCID 204632194-(4-Trifluoromethyl-2-naphthalenyloxy)piperidine

Product 1

HCID 204632036-[4-(4-Trifluoromethyl-2-naphthalenyloxy)-1-piperidyl]-1-(4-methoxyphenyl)-1-hexanone

Procedure

When in the procedure of Example 18, 4-(4-trifluoromethyl-2-naphthalenyloxy)piperidine is substituted for 4-(1-methyl-2-naphthalenyloxy)piperidine and 6-bromo-1-(4-methoxyphenyl)-1-hexanone substituted for 4-chloro-1-(4-fluorophenyl)-1-butanone, 6-[4-(4-trifluoromethyl-2-naphthalenyloxy)-1-piperidyl]-1-(4-methoxyphenyl)-1-hexanone is obtained.

Sources & evidence

ORD record
ord-bf67f7edf97d4b138991dcc419cd55a3
Source dataset
uspto-grants-1984_04
Patent number
US04443462

Reaction notes

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