Sodium cyanoborohydride → HCID 69894679, compound

HRID 1356367Notes

Reaction equation

HRID 1356367 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11]2[C:12]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19][C:13]=3[NH:14][C:15]=2[CH:16]=[CH:17][CH:18]=1.C([BH3-])#N.[Na+]>FC(F)(F)C(O)=O.CO.O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11]2[C@@H:12]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19][C@@H:13]3[NH:14][C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22396794HCID 22396794, compound

Product 1

HCID 69894679HCID 69894679, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A 0° C. solution of 10-(2-methoxyphenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride from above (286 mg, 0.87 mmol) in trifluoroacetic acid (4 mL) was treated with a solution of sodium cyanoborohydride (278 mg 4.42 mmol) in methanol (1 mL). The reaction was allowed to slowly warm to room temperature over 3.8 hours then diluted with water and concentrated in vacuo to remove the majority of acid. The residue was made basic with 15% NaOH, extracted with CH2Cl2 dried over MgSO4 and concentrated in vacuo and passed through a column of silica gel with 1:19 methanol/chloroform with 1% NH4OH to give 91 mg (36%) of a white foam as the title compound: 1H NMR (400 MHz, Acetone-d6) δ 7.34-7.30 (m, 1H), 7.17 (dd, J=7.4 Hz, 1.7 Hz, 1H), 7.06 (d, J=8.3 Hz, 1H), 7.00-6.92 (m, 2H), 6.47 (d, J=7.7 Hz, 1H), 6.42 (d, J=7.6 Hz, 1H), 4.90 (br s, 1H), 4.19-4.14 (m, 1H), 3.78 (s, 3 H), 3.65-3.60 (m, 1H), 2.97-2.93 (m, 1H), 2.64-2.56 (m, 2H) 2.35-2.29 (m, 1H), 1.98-1.94 (m, 1H), 1.48-1.44 (m, 1H), 1.28-1.23 (m, 1H); HRMS (FAB) calcd for C19H22N2O1+H1 295.1810, found 295.1798.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the majority of acid
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c81cf4a2cb64d7186d23355e3a66551
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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