Sodium Hydroxide → HCID 15713338, compound

HRID 704081Notes

Reaction equation

HRID 704081 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[CH3:11][C:12]1[C:24]2[N:23]3[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]3)=[CH:17][C:16]=2[C:15]([NH:25][CH2:26][CH2:27][NH2:28])=[N:14][N:13]=1.C([BH3-])#N.[OH-].[Na+]>CO.[Zn]>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH:28][CH2:27][CH2:26][NH:25][C:15]1[C:16]3[CH:17]=[C:18]4[N:23]([C:24]=3[C:12]([CH3:11])=[N:13][N:14]=1)[CH:22]=[CH:21][CH:20]=[CH:19]4)[CH2:3]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 498716Cyano-borohydrideHCID 20075512N-(4-methylpyridazino[4,5-b]indolizin-1-yl)-1,2-ethanediamine

Product 1

HCID 15713338HCID 15713338, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 3-quinuclidinone hydrochloride (600 mg, 3.7 mmol) in methanol (15 mL) was added a solution of N-(4-methylpyridazino[4,5-b]indolizin-1-yl)-1,2-ethanediamine (900 mg, 3.7 mmol) in methanol (11 mL) over a one minute period at room temperature. After stirring for 5 to 10 minutes, a solution of zinc modified cyanoborohydride (8.7 mL of 0.50M cyanoborohydride in methanol, 4.4 mmol) was added [Kim, et al., J. Org. Chem. 50, 1927 (1985)]. A yellow precipitate formed. After stirring for 4 days at room temperature, 50% sodium hydroxide (1 mL) was added and the solvent was evaporated. The residue was mixed with 4:1 chloroform:methanol (at 20 mL) and filtered through a plug of basic alumina. The filtrate was evaporated and the residue was purified by flash chromatography (alumina, 4:1 chloroform:methanol to 100% methanol) to give the title compound as the free base which was converted to the fumaric acid salt (fumaric acid/ethanol), mp 205°-208° C.

Workup

  1. additionwas added [Kim, et al., J. Org. Chem. 50, 1927 (1985)]
  2. customA yellow precipitate formed
  3. stirringAfter stirring for 4 days at room temperature
  4. customthe solvent was evaporated
  5. additionThe residue was mixed with 4:1 chloroform
  6. filtrationmethanol (at 20 mL) and filtered through a plug of basic alumina
  7. customThe filtrate was evaporated
  8. customthe residue was purified by flash chromatography (alumina, 4:1 chloroform:methanol to 100% methanol)

Sources & evidence

ORD record
ord-d588fe74538b4ef1a911401496c06855
Source dataset
uspto-grants-1991_01
Patent number
US04985560

Reaction notes

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