Sodium cyanoborohydride → HCID 69896056, compound

HRID 2307056Notes

Reaction equation

HRID 2307056 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C:11]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][C:12]=4[NH:13][C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1.C([BH3-])#N.[Na+]>C(O)(C(F)(F)F)=O>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C@@H:11]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][C@@H:12]4[NH:13][C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22396798HCID 22396798, compound

Product 1

HCID 69896056HCID 69896056, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

10-(4-Chlorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride (140mg) was dissolved in TFA (3 ml), cool to 0° C. and sodium cyanoborohydride was added portionwise (150 mg). The reaction mixture stirred two hours, was quenched with 2N NaOH, extracted with EtOAc, dried over MgSO4, filtered and concentrated. The product was dissolved in EtOAc and 1N HCl in Et2O was added. The solvent was evaporated and solid recrystallized from EtOAc/MeOH to provide the title compound: 1H NMR (DMSO-d6) δ 1.31, 1.66, 2.21, 2.7, 2.91, 3.03, 3.27, 4.1-4.4, 6.88, 7.25, 7.52. HRMS (FAB) calcd for C18H21ClN2 (MH+) 299.1315, found 299.1321.

Workup

  1. customwas quenched with 2N NaOH
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe product was dissolved in EtOAc
  7. addition1N HCl in Et2O was added
  8. customThe solvent was evaporated
  9. customsolid recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-faa9d1b496e64337aed4983505ffe831
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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