4-Methylbenzaldehyde → HCID 58933603, compound

HRID 854336Notes

Reaction equation

HRID 854336 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:7])=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C([BH3-])#N.[Na+]>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:18][C:19]3[CH:26]=[CH:25][C:22]([CH3:23])=[CH:21][CH:20]=3)[CH2:14][CH2:15]2)=[O:7])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20114257HCID 20114257, compound

Product 1

HCID 58933603HCID 58933603, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxy-N-piperidin-4-ylmethyl-benzamide (EXAMPLE 154, Step 1) (50 mg, 0.21 mmol) in MeOH (3 mL) was added 4-methylbenzaldehyde (25 mg, 0.21 mmol) and sodium cyanoborohydride (40 mg, 0.64 mmol). The reaction mixture was stirred at rt for 15 h, concentrated and purified by reverse-phase HPLC. (M+H)+=339.2

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-deb45d6792e44463b1539c0c067df08e
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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