Sulfuric acid magnesium salt (1:1) → (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-(4-quinolylmethyl)-4-piperidinamine

HRID 264659Notes

Reaction equation

HRID 264659 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.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:35]=O)=[CH:27][CH:26]=1.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][CH2:35][C:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:25]=[CH:26][CH:27]=2)[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 24083Sulfuric acid magnesium salt (1:1)HCID 780724-QuinolinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 53839030(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine

Product 1

HCID 44288927(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-(4-quinolylmethyl)-4-piperidinamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

1.95 g (5.37 mmol) of (2R,4S)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine are reacted in analogy to Example 2g with 0.93 g (5.90 mmol) of quinoline-4-carboxaldehyde and 0.9 g of magnesium sulfate in 18 ml of toluene and subsequently reduced with 223 mg (5.90 mmol) of sodium borohydride in 18 ml of methanol. The title compound ##STR65## is obtained (2.2 g, 82%) as white foam. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.35, FD-MS: M+ =503, 505, [α]D =19.3 (c=l, MeOH), IR: 1635, 1595, 1565 cm-1.

Sources & evidence

ORD record
ord-afa45daaf264426d958785b83362ca9f
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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