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

HRID 839712Notes

Reaction equation

HRID 839712 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-c7935ee54db748509d0563cda33bc091
Source dataset
uspto-grants-1978_06
Patent number
US04096331

Reaction notes

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