Dimethylamine, hydrochloride → HCID 59597430, compound

HRID 218708Notes

Reaction equation

HRID 218708 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][CH:12]2[C:17]([N:19]([CH2:29][C:30]1[CH:31]=[N:32][N:33]([CH2:35][CH3:36])[CH:34]=1)[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=[O:18].Cl.[CH3:38][NH:39][CH3:40].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:38][N:39]([CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][CH:12]2[C:17]([N:19]([CH2:29][C:30]1[CH:31]=[N:32][N:33]([CH2:35][CH3:36])[CH:34]=1)[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=[O:18]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 59597218HCID 59597218, compound

Product 1

HCID 59597430HCID 59597430, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(4-bromobutoxy)-N-[(l-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.52 g) in acetonitrile (10 mL) were added dimethylamine hydrochloride (0.69 g) and potassium carbonate (1.30 g), and the mixture was heated under reflux for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between water and chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 5-[4-(dimethylamino)butoxy]-N-[(1-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.27 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between water and chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4bc88a56d8ca47e084b951dfe632d9dd
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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