Benzene → Hydrochloride 2-phenyl-2-(3-pyridyl)-2-morpholinoethylbutyronitrile

HRID 328326Notes

Reaction equation

HRID 328326 reaction equation
[NH2-].[Na+].[CH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1([CH:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:16]#[N:17])[CH:14]=CC=[CH:11][CH:10]=1.[O:24]1[CH2:29][CH2:28][N:27](CC[Cl:32])[CH2:26][CH2:25]1>C1(C)C(C)=CC=CC=1>[C:3]1([C:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)([CH:9]([CH2:10][CH2:11][N:27]2[CH2:28][CH2:29][O:24][CH2:25][CH2:26]2)[CH3:14])[C:16]#[N:17])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[ClH:32]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 24533Sodium amideHCID 767274-(2-Chloroethyl)morpholineHCID 270956Phenyl(pyridin-3-yl)acetonitrile

Product 1

HCID 68117851Hydrochloride 2-phenyl-2-(3-pyridyl)-2-morpholinoethylbutyronitrile

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred suspension of 7 parts of sodamide in 90 parts of benzene maintained at 30°-35° C there is added a solution of α-phenyl-3-pyridylacetonitrile, described in U.S. Pat. No. 3,225,054 in 70 parts of benzene. The mixture is then refluxed for 1 hour, cooled and treated by portionwise addition with one equivalent of 2-morpholinoethyl chloride (J. Chem. Soc. pp 505, 1949) in 45 parts of xylene at 30°-40° C. The resulting mixture is refluxed for 2 hours, cooled, filtered and extracted with dilute hydrochloric acid. The acid extract is rendered alkaline and extracted with ether. The ether extract is treated with gaseous hydrogen chloride to yield the hydrochloride 2-phenyl-2-(3-pyridyl)-2-morpholinoethylbutyronitrile.

Workup

  1. temperaturemaintained at 30°-35° C
  2. temperatureThe mixture is then refluxed for 1 hour
  3. temperaturecooled
  4. customat 30°-40° C
  5. temperatureThe resulting mixture is refluxed for 2 hours
  6. temperaturecooled
  7. filtrationfiltered
  8. extractionextracted with dilute hydrochloric acid
  9. extractionThe acid extract
  10. extractionextracted with ether
  11. extractionThe ether extract
  12. additionis treated with gaseous hydrogen chloride

Sources & evidence

ORD record
ord-af5a1698281d46799a851fb2ca2870b1
Source dataset
uspto-grants-1977_04
Patent number
US04017491

Reaction notes

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