HCID 70123891, compound → HCID 9844127, compound

HRID 433925Notes

Reaction equation

HRID 433925 reaction equation
[C:1]([N:5]([C:29](=O)[CH2:30][CH3:31])[C:6]1[C:18]2[C:17]3[CH2:16][CH2:15][CH:14]=[CH:13][C:12]=3[N:11]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:10]=2[N:9]=[C:8]([CH3:28])[CH:7]=1)(=O)[CH2:2][CH3:3]>C1COCC1>[CH2:29]([N:5]([CH2:1][CH2:2][CH3:3])[C:6]1[C:18]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:11]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[C:10]=2[N:9]=[C:8]([CH3:28])[CH:7]=1)[CH2:30][CH3:31]

Participants

3

Reactant 1

HCID 70123891HCID 70123891, compound

Product 1

HCID 9844127HCID 9844127, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dipropionyl-2-methyl-9-(2,4,6-trimethylphenyl)-5H-pyrido[2,3-b]indol-4-amine 1c (312 mg) is refluxed in 8 mL THF with borane-methylsulfide complex (10 M, 1.2 mL) for 10 hours. After cooling the solution, it is carefully quenched with 5 mL of methanol. The resulting solution is refluxed for another 2 hours and then concentrated. The dialkylamine product is purified on silica gel using 20% ethyl acetate in hexanes as eluant to afford N,N-Dipropyl-2-methyl-6,7,8,9-tetrahydro-9-(2,4,6-trimethylphenyl)-5H-pyrido[2,3-b]indol-4-amine (Compound 1) as a white solid, m.p.: 117-118° C.

Workup

  1. temperatureAfter cooling the solution, it
  2. customis carefully quenched with 5 mL of methanol
  3. temperatureThe resulting solution is refluxed for another 2 hours
  4. concentrationconcentrated
  5. customThe dialkylamine product is purified on silica gel using 20% ethyl acetate in hexanes as eluant

Sources & evidence

ORD record
ord-e0e0b4e349924bbe8aa8d0b1c4b52988
Source dataset
uspto-grants-2003_12
Patent number
US06670371B2

Reaction notes

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