Methyl iodide → HCID 14330045, compound

HRID 1651750Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[I-].[CH3:20][N+]1C=CC=CC=1.[BH4-].[Na+]>>[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH2:12][N:13]([CH3:20])[CH2:14][CH2:15][CH:16]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 13596Pyridinium, 1-methyl-, iodide (1:1)

HCID 4311764Sodium borohydride

HCID 14330044HCID 14330044, compound

Product 1

HCID 14330045HCID 14330045, compound

Procedure

Employing the general methods of Examples 4 and 6 above, 10 g (47.3 mmol) of 3-phenyl-1-(3-pyridinyl)-1-propanone were first converted by the action of methyl iodide to the N-methylpyridinium iodide and then reduced by the action of sodium borohydride to produce 3-phenyl-1-(1,2,5,6-tetrahydro-1-methyl-3-pyridinyl)-1-propanone which was isolated as the hydrochloride salt (5.2 g, 58%), mp 195° -197° C.

Sources & evidence

ORD record: ord-99d17be10ad74271a0db275d231d193b
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04929734

Reaction notes

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