Hydrochloric Acid → 4-(Benzyloxy)-1-(2,6-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one hydrochloride

HRID 474915Notes

Reaction equation

HRID 474915 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][C:19]3[C:20]4[CH2:30][N:29]([CH3:31])[CH2:28][CH2:27][CH2:26][C:21]=4[N:22]([CH3:25])[C:23]=3[CH:24]=2)[C:12](=[O:32])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][C:19]3[C:20]4[CH2:30][N:29]([CH3:31])[CH2:28][CH2:27][CH2:26][C:21]=4[N:22]([CH3:25])[C:23]=3[CH:24]=2)[C:12](=[O:32])[CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 498693484-(Benzyloxy)-1-(2,6-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one

Product 1

HCID 668734794-(Benzyloxy)-1-(2,6-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.25 M HCl in MeOH (88 μL) was added to a solution of 4-(benzyloxy)-1-(2,6-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one (23 mg, 0.056 mmol) in MeOH (1.0 mL), and the resulting solution was stirred at ambient temperature for 1.5 h under N2. The mixture was partially concentrated under reduced pressure, diluted with water, and lyophilized to yield the title compound (23 mg, 98%) as a yellow powder; 1H NMR (500 MHz, DMSO-d6) δ 10.02 (br s, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.56 (d, J=7.5 Hz, 1H), 7.49-7.36 (m, 6H), 7.01 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.96 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 4.73-4.71 (m, 1H), 4.52-4.47 (m, 1H), 3.72 (s, 3H), 3.68-3.63 (m, 1H), 3.44-3.41 (m, 1H), 3.16-3.03 (m, 2H), 2.81-2.80 (m, 3H), 2.17-2.01 (m, 2H); ESI MS m/z 414 [M+H]+; HPLC (Method A) 98.3% (AUC), tR=14.3 min.

Workup

  1. concentrationThe mixture was partially concentrated under reduced pressure
  2. additiondiluted with water

Sources & evidence

ORD record
ord-3fffa57f8a464f9ab590d264bfd7dd7c
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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