Sodium triacetoxyborohydride → N-(3,4-dichlorophenyl)-4-[((3R)-1-{[6-(2-methoxyethoxy)pyridin-3-yl]methyl}piperidin-3-yl)methyl]piperazine-1-carboxamide

HRID 603215Notes

Reaction equation

HRID 603215 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:25][O:26][CH2:27][CH2:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][N:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:34][C:33]4[CH:32]=[N:31][C:30]([O:29][CH2:28][CH2:27][O:26][CH3:25])=[CH:37][CH:36]=4)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150670976-(2-Methoxyethoxy)nicotinaldehydeHCID 57656731N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide

Product 1

HCID 57656756N-(3,4-dichlorophenyl)-4-[((3R)-1-{[6-(2-methoxyethoxy)pyridin-3-yl]methyl}piperidin-3-yl)methyl]piperazine-1-carboxamideYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the hydrochloride salt of N-(3,4-dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide (442 mg, 1.00 mmol) in dichloromethane (40 ml) was added 6-(2-methoxyethoxy)nicotinaldehyde (199 mg, 1.00 mmol) and the cloudy mixture stirred at room temperature for 10 minutes. Polymer supported sodium triacetoxyborohydride (555 mg, 1.50 mmol) was added and the reaction stirred at room temperature overnight. The mixture was filtered, the filtrate washed with water (20 ml), organic extract dried (Na2SO4), filtered and evaporated to an oil. Flash column chromatography (10 gram Isolute silica column eluting; CH2Cl2 to 10% MeOH/CH2Cl2) yielded N-(3,4-dichlorophenyl)-4-[((3R)-1-{[6-(2-methoxyethoxy)pyridin-3-yl]methyl}piperidin-3-yl)methyl]piperazine-1-carboxamide (145 mg, 27%) as a white foam.

Workup

  1. additionwas added
  2. stirringthe reaction stirred at room temperature overnight
  3. filtrationThe mixture was filtered
  4. washthe filtrate washed with water (20 ml)
  5. extractionorganic extract
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to an oil
  9. washFlash column chromatography (10 gram Isolute silica column eluting; CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2a4a268b70db4133be688487824544b1
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

Loading…