Benzyl Chloride → HCID 57875949, compound

HRID 1465235Notes

Reaction equation

HRID 1465235 reaction equation
[CH2:1]([N:3]1[CH2:16][CH2:15][C:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FC(F)(F)C([O-])=O>C(NC(C)C)(C)C>[CH2:17]([N:7]1[C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][C:13]=2[C:5]2[CH2:4][N:3]([CH2:1][CH3:2])[CH2:16][CH2:15][C:6]1=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 84468TrifluoroacetateHCID 594550662-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 57875949HCID 57875949, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 7912DiisopropylamineSolvent

Procedure

Preparation of the title compound was carried out according to General Method 5. 2-Ethyl-2,3,4,5-tetrahydro-8-methyl-1H-pyrido[4,3-b]indole (See Example 6) (100 mg, 0.46 mmol) and benzyl chloride (0.11 ml, 0.9 mmol) in diisopropylamine (2 mL) were heated at 80° C. for 12 h to obtain 40 mg of 5-benzyl-2-ethyl-2,3,4,5-tetrahydro-8-methyl-1H-pyrido[4,3-b]indole as a trifluoroacetate salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Sources & evidence

ORD record
ord-aef910018f484cb6901f66f64e72c37e
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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