Sodium hydride → HCID 54046190, compound

HRID 651346Notes

Reaction equation

HRID 651346 reaction equation
[H-].[Na+].[C:3]1([CH2:13][N:14]2[CH2:30][CH2:29][C:17]3([N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][NH:19][C:18]3=[O:28])[CH2:16][CH2:15]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br>CCCCCCC.CN(C)C=O.O>[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N:19]1[C:18](=[O:28])[C:17]2([CH2:29][CH2:30][N:14]([CH2:13][C:3]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:6]=[CH:5][CH:4]=3)[CH2:15][CH2:16]2)[N:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20]1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 783091,7-DibromoheptaneHCID 9907463HCID 9907463, compound2×

Product 1

HCID 54046190HCID 54046190, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8900HeptaneSolvent

Procedure

Sodium hydride, 60% (0.156 g, 3.9 mmol) was suspended in dry heptane (5 ml) and stirred under nitrogen for 5 minutes. The solvent was decanted and dry dimethyl formamide (4 ml) was added. 8-Naphthalen-1-ylmethyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (1.115 g, 3.0 mmol), dissolved in dry dimethyl formamide (11 ml) was added dropwise under cooling in an ice bath. The mixture was stirred at 0° C. for 1 h. The resulting solution of deprotonated 1-phenyl-8-naphthalen-1-ylmethyl-1,3,8-triazaspiro[4.5]decan-4-one was added dropwise to a stirred solution of 1,7-dibromoheptane (3.88 g, 15 mmol) in dimethyl formamide (3 ml) at room temperature and stirring was continued for 1 h. The mixture was then diluted with water (50 ml) and extracted with ethyl acetate (2×30 ml). The combined organic phases were successively washed with water (2×20 ml) and brine (2×20 ml), dried over MgSO4 and evaporated In vacuo. The residue was dissolved in a mixture of tetrahydrofuran (10 ml) and ether (10 ml) and the hydrochloride was precipitated by the dropwise addition of a solution of hydrogen chloride in ether in excess. The precipitate was washed with a 1:1 mixture of tetrahydrofuran and ether and dried, affording 3-(7-bromo-heptyl)-8-naphthalen-1-ylmethyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (1.192 g, 68% yield) as a powder.

Workup

  1. customThe solvent was decanted
  2. additiondry dimethyl formamide (4 ml) was added
  3. additionwas added dropwise
  4. temperatureunder cooling in an ice bath
  5. stirringThe mixture was stirred at 0° C. for 1 h
  6. stirringstirring
  7. waitwas continued for 1 h
  8. extractionextracted with ethyl acetate (2×30 ml)
  9. washThe combined organic phases were successively washed with water (2×20 ml) and brine (2×20 ml)
  10. dry with materialdried over MgSO4
  11. customevaporated In vacuo
  12. dissolutionThe residue was dissolved in a mixture of tetrahydrofuran (10 ml) and ether (10 ml)
  13. customthe hydrochloride was precipitated by the dropwise addition of a solution of hydrogen chloride in ether in excess
  14. washThe precipitate was washed with a 1:1 mixture of tetrahydrofuran and ether
  15. customdried

Sources & evidence

ORD record
ord-253a24e13c914e8c97d338143aafc33f
Source dataset
uspto-grants-2001_08
Patent number
US06277991B1

Reaction notes

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