Methylamine → HCID 22909775, compound

HRID 1379167Notes

Reaction equation

HRID 1379167 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Br)=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:28][N:29](C1C=CC=CN=1)C.C(=O)([O-])[O-].[K+].[K+].CN>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:29][CH3:28])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 218852-DimethylaminopyridineHCID 22909785HCID 22909785, compound

Product 1

HCID 22909775HCID 22909775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.10 g (0.23 mmol) of N-{3-(3,4-dimethylphenyl)propyl}-4-(2-bromoethoxy)-3-methoxyphenylacetamide obtained in step 1 of Example 2 and a catalytic amount of dimethylaminopyridine were dissolved in 50 ml of tetrahydrofuran and 0.048 g (0.35 mmol) of potassium carbonate was added thereto. Then, methylamine was passed through the mixture by bubbling at the temperature ranging from -10° to -20° C. The resultant mixture was stirred at a room temperature for 6 hours. After removing the solvent under a reduced pressure, the residue was subjected to silica gel column chromatography(eluent: ethyl acetate:hexane= 1:1) to obtain the title compound.

Workup

  1. customby bubbling at the temperature
  2. customranging from -10° to -20° C
  3. customAfter removing the solvent under a reduced pressure

Sources & evidence

ORD record
ord-dc32fc43eef0468ab8e5bbca44827be4
Source dataset
uspto-grants-1997_09
Patent number
US05670546

Reaction notes

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