Sulfuric Acid → 4-(Dimethylamino)-2-phenyl-2-(pyridin-2-yl)pentanamide

HRID 1284907Notes

Reaction equation

S(=O)(=O)(O)O.[CH3:6][N:7]([CH:9]([CH3:26])[CH2:10][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:12]#[N:13])[CH3:8].[OH-:27].[Na+]>O>[CH3:6][N:7]([CH:9]([CH3:26])[CH2:10][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:12]([NH2:13])=[O:27])[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

Conc. sulfuric acid (11 ml) was added to 4-(N,N-dimethylamino)-2-phenyl-2-(2-pyridyl)-valeronitrile (6.3 g) at 0° C. and then water (1 ml) was added thereto. After being heated at 90° C. for 3 hours, the mixture was poured into ice-water, adjusted to pH 10 with 10% aqueous sodium hydroxide and extracted with ethyl acetate (50 ml×3). The extracts were combined, and washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The obtained crude crystal was recrystallized from diethyl ether to give 4-(N,N-dimethylamino)-2-phenyl-2-(2-pyridyl)-valeramide (1.89 g). mp 132°-134° C.

Workup

extractionextracted with ethyl acetate (50 ml×3)
washwashed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe obtained crude crystal
customwas recrystallized from diethyl ether

Sources & evidence

ORD record: ord-3d3e266cbb054128b41a436c974df58e
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04564621

Reaction notes

Loading…