Benzoyl chloride → HCID 10368447, compound

HRID 1110031Notes

Reaction equation

HRID 1110031 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C:12]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][N:20]([C:23]5[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][N:24]=5)[CH2:19][CH2:18]4)=[C:13]([CH3:14])[N:8]3[CH2:7][CH2:6][CH2:5]2)[CH:11]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)(Cl)Cl>[C:37]([NH:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C:12]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][N:20]([C:23]5[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][N:24]=5)[CH2:19][CH2:18]4)=[C:13]([CH3:14])[N:8]3[CH2:7][CH2:6][CH2:5]2)[CH:11]=1)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10452955HCID 10452955, compound

Product 1

HCID 10368447HCID 10368447, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2 g of 8-amino-5,6-dihydro-2-methyl-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]-ethyl}-4H-pyrrolo-[3,2,1-ij]quinoline (preparation see Example 20) were dissolved in 25 ml of chloroform. 1.45 ml of triethylamine and then, dropwise, 1.075 g of benzoyl chloride were added to the solution without exceeding a temperature of 20° C. in this process. The reaction mixture was allowed to react at room temperature for hour. To work up the reaction mixture, it was washed with 20 ml of 10% aqueous sodium hydroxide solution until neutral, dried and evaporated. The crude product obtained was purified by chromatography on a small silica gel column using toluene/ethanol 95:5 as the eluent. After recrystallization from ethanol, 0.6 g of 8-benzoylamino-5,6-dihydro-2-methyl-1-{2-[4-(4-methylpyridin-2-yl)-piperazin-1-yl]-ethyl}-4H-pyrrolo[3,2,1-ij]quinoline was obtained as a cream-colored powder. This was converted into the corresponding 0.5-hydrochloride having a melting point of 218° C. as described in Example 3H).

Workup

  1. customa temperature of 20° C.
  2. customto react at room temperature for hour
  3. washwas washed with 20 ml of 10% aqueous sodium hydroxide solution until neutral,
  4. customdried
  5. customevaporated
  6. customThe crude product obtained
  7. customwas purified by chromatography on a small silica gel column
  8. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-09ac677fee4a49e9b1adcb807e02e12d
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

Loading…