(1,5,6,7,8,8a-Hexahydroimidazo[1,5-a]pyridin-3-yl)(phenyl)methanone → HCID 21523491, compound

HRID 918199Notes

Reaction equation

HRID 918199 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.[Cl:18][C:19]1[CH:20]=[C:21]([Mg]Br)[CH:22]=[CH:23][CH:24]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1>>[Cl:18][C:19]1[CH:20]=[C:21]([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:23][CH:24]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([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:30][CH:29]=1

Participants

5

Reactant 3

HCID 71398802(1,5,6,7,8,8a-Hexahydroimidazo[1,5-a]pyridin-3-yl)(phenyl)methanoneHCID 178478127HCID 178478127, compoundHCID 178478191HCID 178478191, compound

Product 2

HCID 21523491HCID 21523491, compoundHCID 21523495HCID 21523495, 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-5517bc82da1147bfa0e96635de569434
Source dataset
uspto-grants-1976_07
Patent number
US03969528

Reaction notes

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