tert-butyl 6-(2-hydroxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate → 2-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanol hydrochloride

HRID 2306953Notes

Reaction equation

HRID 2306953 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]2[CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH2:17][C:5]1=2.[ClH:25].C1C2C3C=CC=CC=3N(CC(O)=O)C=2CCNC1>>[ClH:25].[CH2:13]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]([CH2:3][CH2:2][OH:1])[C:5]=2[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

3

Reactant 2

HCID 22396751tert-butyl 6-(2-hydroxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylateHCID 697964662,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-ylacetic acid hydrochloride

Product 1

HCID 223968312-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanol hydrochlorideYield 48%

Procedure

2-(2,3,4,5-Tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethanol hydrochloride was prepared from tert-butyl 6-(2-hydroxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate by the procedure used to prepare 2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-ylacetic acid hydrochloride in 48% yield. 1H NMR (300 MHz, CDCl3) δ 3.22, 3.37, 3.44-3.52, 3.80, 4.30, 7.07, 7.15, 7.37, 7.48; MS (ESI+) for C14H18N2O m/z 231.3 (M+H)+.

Sources & evidence

ORD record
ord-d54ef535f71b4112a90792656e3683b4
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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