Benzenepropanoyl chloride → HCID 20227416, compound

HRID 1731890Notes

Reaction equation

HRID 1731890 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][C:3]=1[O:14][CH3:15].[C:16]1([CH2:22][CH2:23][C:24](Cl)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1.O1CCCC1>[C:16]1([CH2:22][CH2:23][CH2:24][N:10]2[CH2:11][CH2:12][CH2:13][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:14][CH3:15])[CH:4]=3)[CH2:9]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 20227422HCID 20227422, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20227416HCID 20227416, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by acylation of 995 mg (4.75 mmole) of the 3-(4-fluoro-3-methoxyphenyl)piperidine from Preparation 8, Part B, with 1.2 g (7.13 mmole) of 3-phenylpropionyl chloride in toluene, followed by reduction with 831 mg (21.9 mmole) of lithium aluminum hydride in tetrahydrofuran, substantially according to the procedure of Preparation 3. This afforded 1.49 g (96% yield) of the title compound.

Workup

  1. customsubstantially according to the procedure of Preparation 3

Sources & evidence

ORD record
ord-898aa8d5bde848f6bd45908ca22ef4f0
Source dataset
uspto-grants-1986_11
Patent number
US04623728

Reaction notes

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