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

HRID 474907Notes

Reaction equation

HRID 474907 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[C:19]4[CH2:29][NH:28][CH2:27][CH2:26][CH2:25][C:20]=4[N:21]([CH3:24])[C:22]=3[CH:23]=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:16]=[CH:17][C:18]3[C:19]4[CH2:29][NH:28][CH2:27][CH2:26][CH2:25][C:20]=4[N:21]([CH3:24])[C:22]=3[CH:23]=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 498686704-(benzyloxy)-1-(6-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one

Product 1

HCID 498686694-(Benzyloxy)-1-(6-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(benzyloxy)-1-(6-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one (45 mg, 0.11 mmol) in CH2Cl2 (2.0 mL) was treated with anhydrous 1.0 M HCl in diethyl ether (0.11 mL, 0.11 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 (47 mg, 95%) as an off-white powder: mp 283-287° C., decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.96 (s, 2H), 7.64 (d, J=8.0 Hz, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.48-7.41 (m, 5H), 7.38-7.36 (m, 1H), 6.99 (dd, J=8.5, 2.0 Hz, 1H), 6.10 (dd, J=7.5, 2.5 Hz, 1H), 5.96 (d, J=3.0 Hz, 1H), 5.15 (s, 2H), 4.44-4.43 (m, 2H), 3.71 (s, 3H), 3.45-3.43 (m, 2H), 3.09 (t, J=6.0 Hz, 2H), 2.06-2.04 (m, 2H); ESI MS m/z 400 [M+H]+; HPLC (Method A) 98.2% (AUC), tR=14.3 min.

Workup

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

Sources & evidence

ORD record
ord-de607c7a77fc42b5b9c5649f1eef8f25
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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