Dimethylformamide → 4-amino-N-[1-(2-fluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide

HRID 1676520Notes

Reaction equation

HRID 1676520 reaction equation
N1(O[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:19][CH3:20])[CH:13]=2)C2C=CC=CC=2N=N1.Cl.Cl.[F:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O.O.C(N(CC)CC)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:33][CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][F:24])[CH2:28][CH2:29]2)=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 866374991-(2-Fluoroethyl)piperidin-4-amine dihydrochloride

Product 1

HCID 580151444-amino-N-[1-(2-fluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamideYield 73.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 0.5432 g (1.91 mmole) of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester, 0.4187 g (1.91 mmole) of 1-(2-fluoro-ethyl)-piperidin-4-ylamine dihydrochloride and 8 mL of dimethylformamide was added 1.3316 mL of triethylamine. The mixture was stirred for 25 hours, then taken up in ethyl acetate and twice with 50 mL 0.5 M sodium carbonate, once with 50 mL water, once with 50 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with acetonitrile-methanol-triethylamine (90:10:0.8), to give 0.4159 g 4-amino-N-[1-(2-fluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide.

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with acetonitrile-methanol-triethylamine (90:10:0.8)

Sources & evidence

ORD record
ord-be396edbf58f42189ff16eb47261e2e7
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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