1-Isocyanato-4-methoxybenzene → N-(4-Methoxyphenyl)-3-(2-morpholinoethoxy)-1-pyrrolidinecarboxamide

HRID 1390625Notes

Reaction equation

HRID 1390625 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][O:20][CH:21]2[CH2:25][CH2:24][NH:23][CH2:22]2)[CH2:14][CH2:13]1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([N:23]2[CH2:24][CH2:25][CH:21]([O:20][CH2:19][CH2:18][N:15]3[CH2:14][CH2:13][O:12][CH2:17][CH2:16]3)[CH2:22]2)=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 213331654-[2-(Pyrrolidin-3-yloxy)ethyl]morpholine

Product 1

HCID 13049054N-(4-Methoxyphenyl)-3-(2-morpholinoethoxy)-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Under anhydrous conditions 2.2 g. p-methoxyphenyl isocyanate in 10 ml. of reagent grade benzene was added dropwise to a stirring solution of 3.0 g. (0.15 mole) of 3-(2-morpholinoethoxy) pyrrolidine in 40 ml. of reagent grade benzene. After the addition was complete the reaction mixture was stirred overnight at room temperature and then concentrated at reduced pressure to give the theoretical yield of crude product, which would not crystallize nor form addition salts. The crude product was chromatographed on a column of magnesium silicate to give 1.4 g. of oily product. The nuclear magnetic resonance spectrum and mass spectrum analysis agreed with the proposed structure.

Workup

  1. additionAfter the addition
  2. concentrationconcentrated at reduced pressure
  3. customto give the theoretical yield of crude product, which would not
  4. customcrystallize
  5. customform
  6. additionaddition salts
  7. customThe crude product was chromatographed on a column of magnesium silicate
  8. customto give 1.4 g

Sources & evidence

ORD record
ord-8c398cf1c8fd49efbd33fa2aab672f2a
Source dataset
uspto-grants-1979_02
Patent number
US04139620

Reaction notes

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