Hydrochloric Acid → Hydrochloric Acid

HRID 1677029Notes

Reaction equation

HRID 1677029 reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][C:7]1=2)=[O:4].[ClH:26]>CO.O1CCOCC1>[ClH:26].[CH3:1][O:2][C:3]([CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[CH2:15][NH:16][CH2:17][CH2:18][C:7]1=2)=[O:4].[ClH:26]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57681625tert-butyl 5-methoxycarbonylmethyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 673309635-methoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 5-methoxycarbonylmethyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (377 mg, 1.09 mmol) was dissolved in methanol (15 mL). 4N HCl in 1,4-dioxan (1.5 mL) was added and the mixture stirred at room temperature overnight. The solution was concentrated in vacuo, azeotroped once with toluene and dried under vacuum to give 5-methoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride as an off white solid (314 mg, 100% assuming HCl salt).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customazeotroped once with toluene
  3. customdried under vacuum

Sources & evidence

ORD record
ord-2eb6ed2e16754128a2f911d0f1fcfa98
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

Loading…