(1,5,6,7,8,8a-Hexahydroimidazo[1,5-a]pyridin-3-yl)(phenyl)methanone → HCID 21523494, compound

HRID 918200Notes

Reaction equation

HRID 918200 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][N:4]2[C:3]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[N:2]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.[CH3:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Mg]Br>>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:3]2[N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]3[CH2:1][N:2]=2)[OH:11])=[CH:22][CH:21]=1.[CH3:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:3]1[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]2[CH2:1][N:2]=1)[OH:11]

Participants

5

Reactant 3

HCID 71398802(1,5,6,7,8,8a-Hexahydroimidazo[1,5-a]pyridin-3-yl)(phenyl)methanoneHCID 178424303HCID 178424303, compoundHCID 178491912HCID 178491912, compound

Product 2

HCID 21523494HCID 21523494, compoundHCID 21523496HCID 21523496, compound

Procedure

In an analogous manner, reaction of the ketone of Example 2 with m-chlorophenylmagnesium bromide and p-chlorophenylmagnesium bromide gives respectively α-(m-chlorophenyl)-α-phenyl-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine-3-methanol and α-(p-chlorophenyl)-α-phenyl-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine 3-methanol. Similarly, reaction of the ketone of Example 2 with p-methoxyphenylmagnesium bromide and o-methylphenylmagnesium bromide gives respectively α-(p-methoxyphenyl)-α-phenyl-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine-3-methanol and α-(o-methylphenyl)-α-phenyl-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine-3-methanol.

Sources & evidence

ORD record
ord-9283239f68ae411b9d7bef502acae323
Source dataset
uspto-grants-1976_07
Patent number
US03969528

Reaction notes

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