Sodium cyanoborohydride → 7-chloro-3-(3,5-dimethylphenyl)-4-{1-[4-(4-methoxyphenyl)-butyl]-piperidin-2-yl-methoxy}-1H-quinolin-2-one

HRID 1857605Notes

Reaction equation

HRID 1857605 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][CH:40]=O)=[CH:33][CH:32]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][N:24]3[CH2:40][CH2:39][CH2:38][CH2:37][C:34]3[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:36][CH:35]=3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 104875554-(4-Methoxyphenyl)butanalHCID 221300057-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one

Product 1

HCID 540325717-chloro-3-(3,5-dimethylphenyl)-4-{1-[4-(4-methoxyphenyl)-butyl]-piperidin-2-yl-methoxy}-1H-quinolin-2-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one (prepared essentially as described in Example 10, 34 mg in 3.0 mL dry methanol) was added 18 mg of 4-(4-methoxyphenyl)-butyraldehyde, 150 mg powdered 4 Å molecular sieves and one drop of acetic acid. After 30 minutes, 0.13 mL of a 1M solution of sodium cyanoborohydride in tetrahydrofuran was added and the mixture stirred at room temperature for 18 hours. At this time the reaction mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. Purification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3) gave the title compound, 39 mg.

Workup

  1. filtrationAt this time the reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3)

Sources & evidence

ORD record
ord-4b565d37fcf64e1fbf76b1d070a774de
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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