2-Methoxybenzaldehyde → HCID 57073059, compound

HRID 264698Notes

Reaction equation

HRID 264698 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=O.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[O:26][CH3:25])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 86582-MethoxybenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 53839030(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine

Product 1

HCID 57073059HCID 57073059, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

200 mg (0.551 mmol) of (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine are reacted in analogy to Example 2g with 75 mg (0.551 mmol) of 2-methoxybenzaldehyde and 90 mg magnesium sulfate in 2 ml of toluene and subsequently reduced with 22 mg (0.584 mmol) of sodium borohydride in 2 ml of methanol. The title compound ##STR91## is obtained (170 mg, 64%) as white foam. TLC:methylene chloride/methanol/cone. ammonia (700:50:1) Rf =0.66, FD-MS:M+ =482, 482. IR:1620 cm-1.

Sources & evidence

ORD record
ord-3a0a739b79a94f258482c4c45e99a0d2
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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