Dimethylcarbamoyl Chloride → HCID 60148548, compound

HRID 1843294Notes

Reaction equation

HRID 1843294 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>O1CCCC1.C(OCC)(=O)C>[CH3:21][N:22]([CH3:26])[C:23](=[O:24])[O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 218649361-Benzyl-1,2,3,4-tetrahydroquinolin-7-ol

Product 1

HCID 60148548HCID 60148548, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-benzyl-1,2,3,4-tetrahydroquinolin-7-ol (500 mg, 2.09 mM) in dry tetrahydrofuran (THF, 8 ml) was added to the stirred solution of sodium hydride in dry THF at −10° C. during 5 minutes under nitrogen environment. The reaction mixture was stirred for 30 minutes. Then, N,N-dimethyl carbamoyl chloride (265 mg/ml, 3.14 mM) 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 8k as solid. Yield: 0.796 g, 76.19%.

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-7e5d3e1e005e4091b20ae48a25e36f23
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

Loading…