(5-Chloro-2-methoxy-4-(methylamino)phenyl)(1H-imidazol-1-yl)methanone → 2-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]oct-3-yl 5-chloro-2-methoxy-4-(methylamino)benzoate

HRID 327394Notes

Reaction equation

HRID 327394 reaction equation
[N:1]1([CH2:7][CH:8]2[CH:13]([OH:14])[CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.CCCCCC.[Cl:28][C:29]1[C:30]([NH:44][CH3:45])=[CH:31][C:32]([O:42][CH3:43])=[C:33]([CH:41]=1)[C:34](N1C=CN=C1)=[O:35]>>[Cl:28][C:29]1[C:30]([NH:44][CH3:45])=[CH:31][C:32]([O:42][CH3:43])=[C:33]([CH:41]=1)[C:34]([O:14][CH:13]1[CH:12]2[CH2:11][CH2:10][N:9]([CH2:16][CH2:15]2)[CH:8]1[CH2:7][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[O:35]

Participants

4

Reactant 3

HCID 13492556(5-Chloro-2-methoxy-4-(methylamino)phenyl)(1H-imidazol-1-yl)methanoneHCID 191083992-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]octan-3-olHCID 178418244HCID 178418244, compound

Product 1

HCID 537680002-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]oct-3-yl 5-chloro-2-methoxy-4-(methylamino)benzoate

Procedure

2-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]octan-3-ol cis isomer (2.47 g, 11 mmoles) was treated with n-butyllithium/hexane, and then with 1-[5-chloro-2-methoxy-4-(methylamino)benzoyl]-1H-imidazole, following the procedures described above for the corresponding trans isomer.

Sources & evidence

ORD record
ord-62da3d49246142ad9d00047d7a4af0ad
Source dataset
uspto-grants-1993_12
Patent number
US05273972

Reaction notes

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