Benzaldehyde → HCID 11510932, compound

HRID 603203Notes

Reaction equation

HRID 603203 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]3[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]3)[CH2:16][CH2:15]2)=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10].C(N(CC)C(C)C)(C)C.[CH:36](=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:36]([N:23]1[CH2:24][CH2:25][CH2:26][C@@H:21]([CH2:20][N:17]2[CH2:18][CH2:19][N:14]([C:12]([NH:11][C:6]3[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=3)=[O:13])[CH2:15][CH2:16]2)[CH2:22]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67220603HCID 67220603, compound

Product 1

HCID 11510932HCID 11510932, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperazine-4-carboxamide dihydrochloride (800 mg) in dichloromethane (25 mL) was added N,N-di-iso-propylethylamine (0.94 mL) under argon. The mixture was stirred at room temperature for 5 minutes before benzaldehyde (0.22 mL) and sodium triacetoxyborohydride (573 mg) were added. The reaction mixture was stirred at room temperature under argon for 4 hours. The reaction was quenched with water and then partitioned between dichloromethane and water. The organic extract was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in dichloromethane to give the title compound as a white solid (550 mg, 66%).

Workup

  1. additionwere added
  2. customThe reaction was quenched with water
  3. custompartitioned between dichloromethane and water
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica column chromatography
  9. washeluting with a gradient of 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-e7014d67635447279929ad452930e759
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

Loading…