1-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one → HCID 12150153, compound

HRID 1836675Notes

Reaction equation

HRID 1836675 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[C:14]1([N:20]2[C:24]3([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:23](=[O:30])[NH:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:14]1([N:20]2[C:24]3([CH2:25][CH2:26][N:27]([CH2:8][C:7]4[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=4[C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH2:28][CH2:29]3)[C:23](=[O:30])[NH:22][CH2:21]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 155324822-(1,3-Thiazol-2-yl)benzaldehyde

Product 1

HCID 12150153HCID 12150153, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 2-(2-thiazolyl)benzaldehyde (200 mg, 1.06 mmol) and 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (0.232 mg, 1.00 mmol) in 1,2-dichloroethane (20 mL) was added sodium triacetoxyborohydride (376 mg, 1.79 mmol). The resultant mixture was stirred at room temperature for 18 h, quenched with aqueous NaHCO3 (50 mL) and extracted with CHCl3 (2×50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was dissolved in 1:1 CHCl3:CH3OH (30 mL) and treated with 2 mL of 1 N HCl in Et2O. The HCl salt was precipitated by addition of Et2O, collected by filtration and dried in the vacuum oven at 60° C. for 18 h to yield the product as an amorphous solid.

Workup

  1. customquenched with aqueous NaHCO3 (50 mL)
  2. extractionextracted with CHCl3 (2×50 mL)
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe crude product was dissolved in 1:1 CHCl3
  7. additionCH3OH (30 mL) and treated with 2 mL of 1 N HCl in Et2O
  8. customThe HCl salt was precipitated by addition of Et2O
  9. filtrationcollected by filtration
  10. customdried in the vacuum oven at 60° C. for 18 h

Sources & evidence

ORD record
ord-918881051a294baca162216706de8288
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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