Propionyl chloride → HCID 9845649, compound

HRID 276921Notes

Reaction equation

HRID 276921 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:24])[C:5]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:6]=2[N:23]=1.[C:25](Cl)(=[O:28])[CH2:26][CH3:27]>ClC(Cl)C>[C:25]([N:24]([C:25](=[O:28])[CH2:26][CH3:27])[C:4]1[C:5]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:6]=2[N:23]=[C:2]([CH3:1])[CH:3]=1)(=[O:28])[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 9840045HCID 9840045, compound

Product 1

HCID 9845649HCID 9845649, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-Methyl-6,7,8,9-tetrahydro-9-(2,4,6-trimethylphenyl)-5H-pyrido[2,3-b]indol-4-amine (1b) (470 mg) dissolved in 10 mL dichloroethane is refluxed for 3 hours with propionyl chloride (0.5 mL). The. residual reagents are evaporated under reduced pressure. The crude product is partitioned between aqueous sodium carbonate solution and dichloromethane. The organic extract is dried over sodium sulfate and concentrated. The solid, diacylated product is triturated with hexanes and collected by filtration to afford N,N-Dipropionyl-2-methyl-6,7,8,9-tetrahydro-9-(2,4,6-trimethyl phenyl)-5H-pyrido[2,3-b]indol-4-amine 1c as a white solid.

Workup

  1. customresidual reagents are evaporated under reduced pressure
  2. customThe crude product is partitioned between aqueous sodium carbonate solution and dichloromethane
  3. extractionThe organic extract
  4. dry with materialis dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe solid, diacylated product is triturated with hexanes
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-334e1ece47b047829fef10271dde541e
Source dataset
uspto-grants-2002_03
Patent number
US06355651B1

Reaction notes

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