Benzenepropanoyl chloride → HCID 54564162, compound

HRID 1731889Notes

Reaction equation

HRID 1731889 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[C:15]1([CH2:21][CH2:22][C:23](Cl)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1.O1CCCC1>[C:15]1([CH2:21][CH2:22][CH2:23][N:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 10655338HCID 10655338, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54564162HCID 54564162, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by acylation of 1.0 g (5.2 mmole) of the (R)(-)-3-(3-methoxyphenyl)piperidine from preparation 7, Part C, with 1.3 g (7.8 mmole) of 3-phenylpropionyl chloride in toluene, followed by reduction with 910 mg (24 mmole) of lithium aluminum hydride in tetrahydrofuran, using the procedure of Preparation 3. This afforded 1.9 g of an oil.

Workup

  1. customthe procedure of Preparation 3

Sources & evidence

ORD record
ord-0e878daf17fc4b64a6f9cabcb2f391ad
Source dataset
uspto-grants-1986_11
Patent number
US04623728

Reaction notes

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