Methanesulfonic Acid → 6-Morpholin-4-yl-4-o-tolyl-nicotinamide

HRID 1017489Notes

Reaction equation

HRID 1017489 reaction equation
C([NH:5][C:6](=[O:26])[C:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:11][C:10]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:9][CH:8]=1)(C)(C)C.CS(O)(=O)=O>>[N:20]1([C:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[C:7]([C:6]([NH2:5])=[O:26])=[CH:8][N:9]=2)[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 12167315N-Tert-butyl-6-morpholin-4-YL-4-O-tolyl-nicotinamide

Product 1

HCID 111622966-Morpholin-4-yl-4-o-tolyl-nicotinamideYield 96.8%

Conditions

Temperature
100 °C

Procedure

A mixture of 6.0 g (16.5 mMol) N-tert.-butyl-6-morpholin-4-yl-4-o-tolyl-nicotinamide and 12 ml (185 mMol) methanesulfonic acid was stirred at 100° C. for 5 hours, then poured on ice. The aqueous phase was extracted with tert.-butyl-methylether, brought to pH=10 with NaOH aq. 28% and extracted further with tert.-butyl-methylether. The second organic extracts were dried (Na2SO4) and concentrated to yield 4.75 g (96%) 6-morpholin-4-yl-4-o-tolyl-nicotinamide as a light beige crystalline foam.

Workup

  1. additionpoured on ice
  2. extractionThe aqueous phase was extracted with tert.-butyl-methylether
  3. extractionextracted further with tert.-butyl-methylether
  4. dry with materialThe second organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1a235883ef643f2a30cf5df460ac8c2
Source dataset
uspto-grants-2002_11
Patent number
US06479483B2

Reaction notes

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