tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate → N,N-dimethyl-2-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yloxy)ethanamine

HRID 1677042Notes

Reaction equation

HRID 1677042 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][O:5][C:6]1[C:14]2[NH:13][C:12]3[CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][C:11]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1>Cl>[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][O:5][C:6]1[C:14]2[NH:13][C:12]3[CH2:15][CH2:16][NH:17][CH2:18][C:11]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 57541297tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 57541284N,N-dimethyl-2-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yloxy)ethanamineYield 93%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

tert-Butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (304 mg, 0.85 mmol) was added to methanolic HCl (20 ml, reagent 10) at 0° C. under air. The resulting solution was stirred at room temperature for 19 hours. The solvent was removed under reduced pressure to afford N,N-dimethyl-2-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yloxy)ethanamine (205 mg, 93%) as a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8376374c1b6746afa450af7bae1cf58c
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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