Hydrochloric Acid → 4-(Benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one hydrochloride

HRID 474900Notes

Reaction equation

HRID 474900 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][C:20]=4[N:21]3[CH3:24])=[CH:17][CH:16]=2)[C:11](=[O:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31].C(OCC)C>C(Cl)Cl>[ClH:31].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][C:20]=4[N:21]3[CH3:24])=[CH:17][CH:16]=2)[C:11](=[O:30])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 498694884-(Benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one

Product 1

HCID 668736524-(Benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one (30 mg, 0.075 mmol) in CH2Cl2 (1.0 mL) was treated with anhydrous 1.0 M HCl in diethyl ether (75 μL, 0.075 mmol), and the resulting solution was stirred at ambient temperature for 1 h. The solution was concentrated to dryness, diluted with H2O and lyophilized to yield the title compound (32 mg, 99%) as a yellow powder: mp 210-218° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.04 (s, 2H), 7.59-7.55 (m, 2H), 7.48-7.41 (m, 5H), 7.38-7.36 (m, 1H), 6.97 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.97 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 4.53 (s, 2H), 3.74 (s, 3H), 3.49-3.47 (m, 2H), 2.97 (t, J=5.0 Hz, 2H), 1.99-1.97 (m, 2H); ESI MS m/z 400 [M+H]+; HPLC (Method A) 97.9% (AUC), tR=14.8 min.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. additiondiluted with H2O

Sources & evidence

ORD record
ord-665f9d5d2bf54f8193cc280768ab3e59
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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