Tetrahydrofuran → 4-(4-Morpholino-3-nitrophenyl)-4-(cyano)-4-(morpholino)-3-methylbutyronitrile

HRID 255889Notes

Reaction equation

HRID 255889 reaction equation
[C:1](#[N:5])/[CH:2]=[CH:3]/[CH3:4].O1CCCC1.[O:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[C:22]([N+:32]([O-:34])=[O:33])[CH:21]=2)[C:18]#[N:19])[CH2:13][CH2:12]1.[OH-].[K+]>O.CO>[O:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([C:17]([C:18]#[N:19])([N:14]3[CH2:15][CH2:16][O:11][CH2:12][CH2:13]3)[CH:3]([CH3:4])[CH2:2][C:1]#[N:5])=[CH:21][C:22]=2[N+:32]([O-:34])=[O:33])[CH2:27][CH2:28]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14797Potassium HydroxideHCID 637921CrotononitrileHCID 21855724alpha-Morpholino-alpha(4-morpholino-3-nitrophenyl)-acetonitrile

Product 1

HCID 201649914-(4-Morpholino-3-nitrophenyl)-4-(cyano)-4-(morpholino)-3-methylbutyronitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 8.0 parts of crotononitrile in 20 parts by volume of tetrahydrofuran is added to a stirred mixture of 16.5 parts of α-morpholino-α(4-morpholino-3-nitrophenyl)-acetonitrile in 150 parts by volume of tetrahydrofuran and 1.5 parts of potassium hydroxide in 5 parts by volume of methanol at room temperature under an atmosphere of nitrogen. The reaction mixture is stirred for a further 6 hours, diluted with 500 parts by volume of water and extracted with 4×250 parts by volume of ethyl acetate. The combined organic extracts are dried over magnesium sulphate and concentrated under vacuum. The resulting crude product is triturated with a mixture of 50 parts by volume of ethyl acetate and hexane. The solid product is collected, washed with ethyl acetate and dried at 80° under vacuum to give 4-(4-morpholino-3-nitrophenyl)-4-(cyano)-4-(morpholino)-3-methylbutyronitrile having melting point 175°-177° C.

Workup

  1. extractionextracted with 4×250 parts by volume of ethyl acetate
  2. dry with materialThe combined organic extracts are dried over magnesium sulphate
  3. concentrationconcentrated under vacuum
  4. customThe resulting crude product is triturated with a mixture of 50 parts by volume of ethyl acetate and hexane
  5. customThe solid product is collected
  6. washwashed with ethyl acetate
  7. customdried at 80° under vacuum

Sources & evidence

ORD record
ord-34f3dbb82e4147ccac19e4dc74d3b950
Source dataset
uspto-grants-1987_10
Patent number
US04699908

Reaction notes

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