Sodium cyanoborohydride → HCID 10062837, compound

HRID 1743851Notes

Reaction equation

HRID 1743851 reaction equation
[Cl:1][C:2]1[C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:8]3[C:9]=2[C:5]([C:6]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:7]=23)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:8]3[C:9]=2[C:5]([CH:6]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:7]23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10446856HCID 10446856, compound

Product 1

HCID 10062837HCID 10062837, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-chloro-2,3,4,5,10,11,12,13-octahydro-1H,9H-cyclohepta[b][1,4]diazocino[7,8,1-hi]indole (0.20 g, 0.69 mmole) in acetic acid (50 mL) was added excess sodium cyanoborohydride (0.21 g, 3.45 mmole) and the reaction mixture was stirred at room temperature for 5 hours. The solvent was removed in vacuo and the residue was diluted with methylene chloride (200 mL) and washed with aqueous sodium hydroxide (1N, 150 mL), saturated sodium chloride (150 mL), dried (sodium sulfate) and concentrated. Purification by flash column chromatography (silica gel, 1.5% to 5% methanol in methylene chloride) provided 67 mg of the title compound. This compound was treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 168-170° C. MS (ESI) m/z 291 ([M+H]+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with methylene chloride (200 mL)
  3. washwashed with aqueous sodium hydroxide (1N, 150 mL), saturated sodium chloride (150 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (silica gel, 1.5% to 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-36adca6bc76a43aabbb2ed178f3a9f32
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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