1,2-Dichloroethane → HCID 69609124, compound

HRID 1836685Notes

Reaction equation

HRID 1836685 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:18]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:47]CCCl>>[ClH:47].[O:18]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27][N:14]1[CH2:13][CH2:12][C:11]2([N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][NH:9][C:10]2=[O:17])[CH2:16][CH2:15]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 88060o-PhenoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69609124HCID 69609124, compound

Procedure

To a mixture of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (291 mg, 1.26 mmol) and 2-phenoxybenzaldehyde (299 mg, 1.50 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (454 mg, 2.14 mmol). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 20 h. The reaction mixture was then quenched with 1N aqueous NaHCO3 and extracted with CHCl3 (100 mL). The combined extracts were dried over Na2SO4, filtered and concentrated. The isolated solid was purified by flash chromatography on silica gel to yield the title compound as a free base.

Workup

  1. customThe reaction mixture was then quenched with 1N aqueous NaHCO3
  2. extractionextracted with CHCl3 (100 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe isolated solid was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-12365dd7326f4c42a8a943f412dc63fd
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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