Benzaldehyde → N*2*-Benzyl-N*1*-(8-methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamine

HRID 1966541Notes

Reaction equation

HRID 1966541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[NH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][NH2:17].[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[BH4-].[Na+]>>[CH2:24]([NH:17][CH2:16][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:14][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[N:11]=[C:10]([CH3:13])[CH:9]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 70276090N*1*-(8-Methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamine

Product 1

HCID 59474813N*2*-Benzyl-N*1*-(8-methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamineYield 11%

Conditions

Temperature
60 °C

Procedure

N*1*-(8-Methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamine (Example 75, 150 mg, 0.488 mmole) and benzaldehyde were stirred at RT for 20 hrs. Molecular sieve (4A) was added and the mixture was heated to 60° C. within 2 hrs. NaBH4 was added and the mixture was stirred for 1 h at RT. The resulting mixture was filtered and extracted with dichloromethane. The organic phases were dried and concentrated. The residue was purified using preparative HPLC (RP-18, water/acetonitrile) to obtain the product (21 mg, 11%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. extractionextracted with dichloromethane
  3. customThe organic phases were dried
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-27c07801857346188322936edc9b65d5
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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