Propionyl chloride → HCID 9845649, compound

HRID 433924Notes

Reaction equation

HRID 433924 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 white solid.

Workup

  1. customThe residual 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-a1c8e10dee5543fd899e9989e00a31fe
Source dataset
uspto-grants-2003_12
Patent number
US06670371B2

Reaction notes

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