Hydrochloric Acid → 1,2,3,4,4a,5,6,7-Octahydropyrazino[1,2-a][1,5]benzodiazepine

HRID 1035280Notes

Reaction equation

HRID 1035280 reaction equation
[CH2:1]1[N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][CH2:10][CH2:11][CH:5]2[CH2:4][N:3](C(OC(C)(C)C)=O)[CH2:2]1.Cl>ClCCl>[CH2:1]1[N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][CH2:10][CH2:11][CH:5]2[CH2:4][NH:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58284934Tert-butyl 1,2,4a,5,6,7-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepine-3(4h)-carboxylate

Product 1

HCID 497644211,2,3,4,4a,5,6,7-Octahydropyrazino[1,2-a][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 17A (50 mg, 0.165 mmol) in dichloromethane (5 mL) was added HCl (4 M in dioxane, 824 μL, 3.30 mmol). After reaction completion as indicated by LC/MS analysis, the solution was concentrated and purified by preparative HPLC to afford the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 7.48 (t, J=7.48 Hz, 1H), 7.36 (d, J=7.02 Hz, 1H), 7.19-7.29 (m, 2H), 3.47-3.57 (m, 1H), 3.35-3.44 (m, 2H), 3.10-3.35 (m, 6H), 1.76 (s, 2H); MS (ESI) m/z 204.0 (M+H)+.

Workup

  1. customAfter reaction completion
  2. concentrationthe solution was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3524c9092e8e418ebff2916ac80730b7
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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