Benzyl Chloride → 5-benzyl-2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 509678Notes

Reaction equation

HRID 509678 reaction equation
[CH2:1]([N:3]1[CH2:15][CH2:14][C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.FC(F)(F)C([O-])=O>C(NC(C)C)(C)C>[CH2:16]([N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:5]2[CH2:4][N:3]([CH2:1][CH3:2])[CH2:15][CH2:14][C:6]1=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 84468TrifluoroacetateHCID 5888242-Ethyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Product 1

HCID 578763505-benzyl-2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 34.4%

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-1H-pyrido[4,3-b]indole (See Example 5) (100 mg, 0.5 mmol), benzyl chloride (158 mg, 1.25 mmol) in diisopropylamine (2 mL) were heated at 80° C. for 12 h to obtain 50 mg of 5-benzyl-2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as 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-6c2b1759292d41c585271a106048259f
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

Loading…