Acetyl chloride → HCID 11743554, compound

HRID 1110030Notes

Reaction equation

HRID 1110030 reaction equation
[OH: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:30](Cl)(=[O:32])[CH3:31].C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:30]([O: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:32])[CH3:31]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 10475519HCID 10475519, compound

Product 1

HCID 11743554HCID 11743554, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.2 g of 5,6-dihydro-2-methyl-8-hydroxy-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-4H-pyrrolo[3,2,1-ij]quinoline (preparation see Example 6), 0.884 g of acetyl chloride and 0.78 ml of triethylamine were heated under reflux for 5 hours in 15 ml of toluene. To work up the reaction mixture it was added to 50 ml of 10% strength aqueous sodium hydroxide solution. The toluene phase was separated and washed with water until neutral and concentrated. 2 g of crude product were obtained, which was purified by chromatography on a small silica gel column using first dichloromethane and then dichloromethane/ethanol 98:2. 1.8 g of oily title compound were obtained. This was converted into its hydrochloride as described in Example 1H). 1.72 g of 8-acetoxy-5,6-dihydro-2-methyl-1-{2-[4-(4-methylpyridin-2-yl)piperazin-1-yl]ethyl}-4H-pyrrolo-[3,2,1-ij]quinoline 2 HCl 22.5 H2O having a melting point of 220° C. were obtained.

Workup

  1. customThe toluene phase was separated
  2. washwashed with water until neutral and
  3. concentrationconcentrated
  4. custom2 g of crude product were obtained
  5. customwhich was purified by chromatography on a small silica gel column

Sources & evidence

ORD record
ord-86bd7bdfb1f5463e9d581afb876787bc
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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