Ethyl Acetate → HCID 9950442, compound

HRID 1835085Notes

Reaction equation

HRID 1835085 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.[NH:18]1[C:26]2[CH2:25][CH2:24][CH2:23][C:22](=[O:27])[C:21]=2[CH:20]=[CH:19]1.[OH-].[Na+].C(OCC)(=O)C>CS(C)=O.ClCCl>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][N:18]2[C:26]3[CH2:25][CH2:24][CH2:23][C:22](=[O:27])[C:21]=3[CH:20]=[CH:19]2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 9950442HCID 9950442, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine (7.30 g) was dissolved in DMSO (30 mL), then slowly added to 1,5,6,7-tetrahyro-indol-4-one (30.1 mmol) which was pretreated with sodium hydroxide (31.6 mmol) in DMSO (15 mL) for 0.5 h with slight heat. The reaction was left under heat and was monitored by TLC (ethyl acetate: dichloromethane, 1:1). After completion (8 h), the reaction mixture was poured in ice water (300 mL) and extracted with dichloromethane twice, dried with sodium sulfate and solvent removed under vacuum. Flash chromatography (ethyl acetate: dichloromethane, 1:4) yielded an oil, NEO-377 (7.25 g).

Workup

  1. waitThe reaction was left
  2. temperatureunder heat
  3. extractionextracted with dichloromethane twice
  4. dry with materialdried with sodium sulfate and solvent
  5. customremoved under vacuum
  6. customFlash chromatography (ethyl acetate: dichloromethane, 1:4) yielded an oil

Sources & evidence

ORD record
ord-746dee0d9f094a7785aabc7a6a3dfb55
Source dataset
uspto-grants-2004_08
Patent number
US06770638B2

Reaction notes

Loading…