Dimethylamine → HCID 21711173, compound

HRID 651347Notes

Reaction equation

HRID 651347 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2([CH2:15][CH2:14][N:13]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:6]1.[CH3:33][NH:34][CH3:35].[I-].[Na+]>C(O)C>[ClH:1].[ClH:1].[CH3:33][N:34]([CH3:35])[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2([CH2:15][CH2:14][N:13]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 54501858HCID 54501858, compound

Product 1

HCID 21711173HCID 21711173, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3-chloropropyl)-8-naphthalen-1-ylmethyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (0.145 g, 0.30 mmol), prepared using the procedure described in Example 13, was added to a 33% solution of dimethylamine in ethanol. Sodium iodide (0.045 g, 0.3 mmol) was added and the mixture was stirred at room temperature for 24 h. Salts were separated by filtration and the filtrate was evaporated in vacuo. The residue was purified by flash chromatography on silica gel using dichloromethane/ethyl acetate 1:1 containing 2.5% triethylamine as the eluent. The pooled pure fractions were evaporated and the residue dissolved in tetrahydrofuran (5 ml) and the hydrochloride was precipitated by the dropwise addition of a solution of hydrogen chloride in ether in excess. The precipitate was collected by filtration and dried, affording the title compound (148 mg, 93% yield) as a powder.

Workup

  1. customSalts were separated by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel
  4. customThe pooled pure fractions were evaporated
  5. dissolutionthe residue dissolved in tetrahydrofuran (5 ml)
  6. customthe hydrochloride was precipitated by the dropwise addition of a solution of hydrogen chloride in ether in excess
  7. filtrationThe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-8d35389f921947ddbe7143333c4b6598
Source dataset
uspto-grants-2001_08
Patent number
US06277991B1

Reaction notes

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