Dimethylcarbamoyl Chloride → HCID 60161671, compound

HRID 1843303Notes

Reaction equation

HRID 1843303 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[H-].[Na+].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20]>O1CCCC1.C(OCC)(=O)C>[CH3:17][N:18]([CH3:22])[C:19](=[O:20])[O:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][CH2:5][N:4]2[CH2:1][C:2]#[CH:3])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 86704185HCID 86704185, compound

Product 1

HCID 60161671HCID 60161671, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(prop-2-ynyl)-1,2,3,4-tetrahydroquinolin-7-ol (400 mg, 2.14 mM) in dry tetrahydrofuran (THF; 5 mL) was added to the stirred solution of sodium hydride in dry THF at −10° C. during 5 minutes under nitrogen environment at room temperature (25° C.). The reaction mixture was stirred for 30 minutes. Then, N,N-dimethyl carbamoyl chloride (0.25 mL) was added to the stirring reaction mixture. The mixture was stirred further for 7 hours during which the temperature was allowed to reach the room temperature (35° C.). The reaction mixture was diluted with ethyl acetate, washed with water, and dried over sodium sulphate. The combined fractions of ethyl acetate were concentrated under vacuum and chromatographed using ethyl acetate:hexane (1:49) to afford 10g as solid. Yield: 414 mg, 75.6%.

Workup

  1. stirringThe mixture was stirred further for 7 hours during which the temperature
  2. customthe room temperature (35° C.)
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationThe combined fractions of ethyl acetate were concentrated under vacuum
  6. customchromatographed

Sources & evidence

ORD record
ord-0669710639a24c9c969fc68f68cfa57b
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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