Hydrochloric Acid → Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

HRID 2236093Notes

Reaction equation

HRID 2236093 reaction equation
C(OC([N:8]1[CH2:26][CH2:25][C:11]2[N:12]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:27]>C(OCC)(=O)C>[ClH:27].[CH2:9]1[C:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:11]=2[CH2:25][CH2:26][NH:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71063767Ethyl (2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate

Product 1

HCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of ethyl (2-tert.-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate (8.45 g, 23.6 mmol) in ethyl acetate (80 ml) is treated with a solution of 3M HCl in ethyl acetate (39.3 ml). After stirring at room temperature for 3 h, the solvent is removed in vacuo and the residue azeotroped twice with toluene. The crude product is suspended in diethyl ether, filtered off, washed with diethyl ether and dried. Finally, pure title compound is obtained as beige solid (5.49 g) in 79% yield. tR (LC-2) 1.41 min; ESL-MS (positive ion): m/z 259.33 [M+H]+ (calcd 258.32 for C15H18N2O2).

Workup

  1. customthe solvent is removed in vacuo
  2. customthe residue azeotroped twice with toluene
  3. filtrationfiltered off
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-f773c64b2dfe498e933999e41fe0dbf4
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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