Acetone → HCID 86587529, compound

HRID 1635038Notes

Reaction equation

HRID 1635038 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1.C(N(CC)CC)C.[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[C:30]2[CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C[C:43](C)=[O:44]>C(#N)C>[ClH:1].[CH3:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:43]([N:39]2[CH2:40][CH2:41][CH:36]([C:30]3[C:29]4[C:33](=[CH:34][CH:35]=[C:27]([F:26])[CH:28]=4)[NH:32][CH:31]=3)[CH2:37][CH2:38]2)=[O:44])=[CH:7][C:6]=1[N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471Triethylamine2×HCID 117699295-fluoro-3-(piperidin-4-yl)-1H-indoleHCID 69747384HCID 69747384, compound

Product 1

HCID 86587529HCID 86587529, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-methoxy-3-(4-methylpiperazin-1-yl)aniline dihydrochloride (2.65 g; 9 mmol), triethylamine (4.5 ml; 31.5 mmol) and N,N′-carbonyldiimidazole (1.6 g; 10 mmol) in 125 ml of acetonitrile is stirred at room temperature for 3 hours. A suspension of 2.0 g (9 mmol) of 5-fluoro-3-piperidin-4-yl-1H-indole and 1.3 ml (9 mmol) of triethylamine in 125 ml of acetonitrile is added to the mixture and it is stirred at room temperature for a further 12 hours. After customary working up, the residue is dissolved in acetone and the hydrochloride is precipitated using 1N HCl. By recrystallization from ethanol/diethyl ether, 4-(5-fluoro-1H-indole-3-yl)piperidine-1-carboxylic acid [4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]amide hydrochloride is obtained

Workup

  1. additionis added to the mixture and it
  2. customthe hydrochloride is precipitated
  3. customBy recrystallization from ethanol/diethyl ether

Sources & evidence

ORD record
ord-05b6366d641c462495ca3144e69871b2
Source dataset
uspto-grants-2003_01
Patent number
US06509340B1

Reaction notes

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