Triethylamine → 6-(N,N-dimesylamino)-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 35672Notes

Reaction equation

HRID 35672 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:12][CH2:11][C:10]2=[O:21].C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[S:2]([N:6]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:12][CH2:11][C:10]2=[O:21])[S:2]([CH3:1])(=[O:4])=[O:3])([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 212947846-Amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 212948086-(N,N-dimesylamino)-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 95.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (2.004 g) in methylene chloride (5 ml) was added dropwise to a solution of 6-amino-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.526 g) and triethylamine (2.121 g) in methylene chloride (15 ml) with ice cooling over a period of 15 minutes and stirred for further 1 hour. The mixture was diluted with chloroform, washed successively with 10% hydrochloric acid, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residual solid was washed with methanol and dried to give 6-(N,N-dimesylamino)-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.51 g).

Workup

  1. washwashed successively with 10% hydrochloric acid, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. washThe residual solid was washed with methanol
  5. customdried

Sources & evidence

ORD record
ord-67be754388f94016a5a9572857815fed
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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