N-methyl-2-pyrrolidone → Vilazodone

HRID 2408766Notes

Reaction equation

HRID 2408766 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[NH:8][CH:7]=1.[N:17]1([C:23]2[CH:24]=[CH:25][C:26]3[O:30][C:29]([C:31]([NH2:33])=[O:32])=[CH:28][C:27]=3[CH:34]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O.C(#N)C>[CH:11]1[C:12]([C:15]#[N:16])=[CH:13][C:14]2[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:20]3[CH2:21][CH2:22][N:17]([C:23]4[CH:24]=[CH:25][C:26]5[O:30][C:29]([C:31]([NH2:33])=[O:32])=[CH:28][C:27]=5[CH:34]=4)[CH2:18][CH2:19]3)=[CH:7][NH:8][C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 98347195-(Piperazin-1-yl)benzofuran-2-carboxamide2×HCID 98811233-(4-Chlorobutyl)-5-cyanoindole

Product 1

HCID 6918314Vilazodone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-(4-chlorobutyl)-1H-indole-5-carbonitrile (1.01 g, 1.0 equiv.), 5-(piperazin-1-yl)benzofuran-2-carboxamide (1.10 g, 1.03 equiv.), diisopropylethyl amine (DIPEA, 0.64 g, 1.16 equiv.), and N-Methyl-2-pyrrolidone (NMP, about 40 mL) are charged to a suitable vessel. It is to be noted that 5-(piperazin-1-yl)benzofuran-2-carboxamide may be produced using methods known in the art (see, e.g., U.S. Pat. No. 5,977,112). The mixture is heated and stirred until the reaction is complete. Acetonitrile (about 40 mL) and water (about 40 mL) are charged while maintaining elevated temperature. The mixture is cooled slowly to precipitate vilazodone, filtered, and the wet cake is washed with acetonitrile/water and then with acetonitrile. The wet product is dried to provide crude vilazodone. Purification is carried out via conventional means known in the art, e.g., filtration and precipitation.

Workup

  1. custommay be produced
  2. temperatureThe mixture is heated
  3. temperaturewhile maintaining elevated temperature
  4. temperatureThe mixture is cooled slowly
  5. customto precipitate vilazodone
  6. filtrationfiltered
  7. washthe wet cake is washed with acetonitrile/water
  8. customThe wet product is dried

Sources & evidence

ORD record
ord-cdf8ad27337641d986426f61f9287616
Source dataset
uspto-grants-2014_08
Patent number
US08815870B2

Reaction notes

Loading…