Acetyl chloride → 1-(2-Acetyl-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one

HRID 2365406Notes

Reaction equation

HRID 2365406 reaction equation
Cl.Cl.[CH3:3][N:4]1[C:12]2[CH:11]=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15][C:14]3=[O:27])[CH:9]=[CH:8][C:7]=2[C:6]2[CH2:28][NH:29][CH2:30][CH2:31][C:5]1=2.[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:32]([N:29]1[CH2:30][CH2:31][C:5]2[N:4]([CH3:3])[C:12]3[CH:11]=[C:10]([N:13]4[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:15][C:14]4=[O:27])[CH:9]=[CH:8][C:7]=3[C:6]=2[CH2:28]1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 521913N,N-Diethyl-2-propanamineHCID 679694221-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one dihydrochloride

Product 1

HCID 573833361-(2-Acetyl-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one dihydrochloride (170 mg, 0.368 mmol), acetyl chloride (˜120 μL, 1.5 mmol) and i-PrNEt2 (400 μL, 2.23 mmol) were combined in methylene chloride (20 mL) and stirred for 16 h. Sodium bicarbonate solution (4 mL) was added and the organics removed and concentrated. The residue was purified by flash chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 85% methylene chloride over 30 min) to provide the title compound as a white solid; 1H NMR (500 MHz, DMSO-d6) δ 11.86 (m, 1H), 7.50-7.48 (dd, J=8.3, 5.0 Hz, 1H), 7.40-7.31 (m, 5H), 7.31-7.26 (m, 1H), 6.98-6.95 (overlapping ddd, J=4.0, 1.5 Hz, 1H), 4.65 (d, J=11.2 Hz, 2H), 4.23-3.97 (m, 3H), 3.97-3.75 (m, 3H), 3.64-3.61 (m, 3H), 3.57-3.42 (m, 4H), 3.19-3.08 (m, 2H), 2.93-2.87 (m, 1H), 2.82-2.77 (m, 1H), 2.13-2.11 (2×s, 3H); ESI MS m/z 431 [M+H]+; HPLC (Method B)>99% (AUC), tR=13.8 min.

Workup

  1. customthe organics removed
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (12 g ISCO column
  4. washeluting with methylene chloride

Sources & evidence

ORD record
ord-bd205d17aae94dac8ef1ce281b60bff8
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

Loading…