Sodium cyanoborohydride → HCID 10040741, compound

HRID 1743847Notes

Reaction equation

HRID 1743847 reaction equation
[Cl:1][C:2]1[C:10]2[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][N:8]3[C:9]=2[C:5]([C:6]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][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][N:13]([CH3:16])[CH2:14][CH2:15][N:8]3[C:9]=2[C:5]([CH:6]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:7]23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10425048HCID 10425048, compound

Product 1

HCID 10040741HCID 10040741, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-chloro-3-methyl-2,3,4,5,10,11,12,13-octahydro-1H,9H-cyclohepta[b][1,4]diazocino[7,8,1-hi]indole (0.20 g, 0.66 mmole) in acetic acid (50 mL) was added excess sodium cyanoborohydride (0.21 g, 3.3 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 ethyl acetate (200 mL) and washed with saturated sodium bicarbonate (150 mL), saturated sodium chloride (150 mL), dried (sodium sulfate) and concentrated. Purification by flash column chromatography (silica gel, ethyl acetate:hexanes 3:2) provided 0.17 g of the title compound. This was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 190-193° C. MS (ESI) m/z 305 ([M+H]+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate (200 mL)
  3. washwashed with saturated sodium bicarbonate (150 mL), saturated sodium chloride (150 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (silica gel, ethyl acetate:hexanes 3:2)

Sources & evidence

ORD record
ord-fbb04a5ecd4d4790863b6fc19a5ff1a0
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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