Ethanol hydrochloride → (6,7-Dimethoxy-3-styryl-quinoxalin-2-yl)-(3-piperidin-4-yl-propyl)-amine hydrocloride

HRID 1250236Notes

Reaction equation

HRID 1250236 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]2[C:27]([CH:28]=[CH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:26][C:25]3[C:20](=[CH:21][C:22]([O:38][CH3:39])=[C:23]([O:36][CH3:37])[CH:24]=3)[N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:40].CCO>>[ClH:40].[CH3:37][O:36][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:38][CH3:39])[N:19]=[C:18]([NH:17][CH2:16][CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:27]([CH:28]=[CH:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[N:26]2

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 701643374-[3-(6,7-Dimethoxy-3-styryl-quinoxalin-2-ylamino)-propyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131723085(6,7-Dimethoxy-3-styryl-quinoxalin-2-yl)-(3-piperidin-4-yl-propyl)-amine hydrocloride

Procedure

A solution of the product from Step A above (150 mg, 0.28 mmol) in conc HCl/EtOH (1:2 mixture, 3 mL) was stirred for 2 h at room temperature. The reaction mixture was concentrated under vacuum and the residue was azeotroped twice with ethanol to give the desired product as an amorphous solid. API-MS: 433 (M+1). 1H NMR (300 MHz, d4-MeOH): d 8.0 (d, 2 H), 7.75 (d, 2 HO, 7.66 (d, 2 H), 7.4 (m), 4.0 (s, 3 H), 3.96 (s, 3 H)m 3.65 (t, 2 H), 3.28 (m, 2 H), 2.96 (t, 2 H), 2.0-1.2 (m).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was azeotroped twice with ethanol

Sources & evidence

ORD record
ord-3382c65576f64d18b51a3ff2effa2999
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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