Sodium cyanoborohydride → HCID 10423616, compound

HRID 1743882Notes

Reaction equation

HRID 1743882 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:10]3[C:11]=2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=13.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:10]3[C:11]=2[C:3]=1[CH:4]1[CH:9]3[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10423507HCID 10423507, compound

Product 1

HCID 10423616HCID 10423616, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 8-chloro-2,3,4,5,9,10,11,12-octahydro-1H-[1,4]diazocino[7,8,1-jk]carbazole (2.2 g, 8.00 mmole) in acetic acid (200 mL) was added sodium cyanoborohydride (95 wt. %, 2.5 g, 40.0 mmole) and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with methylene chloride (400 mL) and washed with aqueous sodium hydroxide (1N, 300 mL), saturated sodium chloride (300 mL), dried (sodium sulfate) and concentrated. Purification by flash column chromatography (silica gel, 1.5% to 5% methanol in methylene chloride) provided 1.67 g of the title compound. 0.116 g of the compound was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 199-200° C. MS (ES) m/z 277.1 ([M+H]+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with methylene chloride (400 mL)
  3. washwashed with aqueous sodium hydroxide (1N, 300 mL), saturated sodium chloride (300 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-10705e1d80994ffda1290a90b19d8c6b
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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