Potassium Carbonate → 3-(2-Morpholinoethoxy)-1-(3,4,5-trimethoxyphenylacetyl) pyrrolidine Hemihydrate

HRID 1390626Notes

Reaction equation

HRID 1390626 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14](Cl)=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[O:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[OH2:2].[O:17]1[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][O:25][CH:26]2[CH2:30][CH2:29][N:28]([C:14](=[O:15])[CH2:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH2:27]2)[CH2:21][CH2:22]1.[O:17]1[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][O:25][CH:26]2[CH2:30][CH2:29][N:28]([C:14](=[O:15])[CH2:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH2:27]2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110321242-(3,4,5-trimethoxyphenyl)acetyl ChlorideHCID 213331654-[2-(Pyrrolidin-3-yloxy)ethyl]morpholine

Product 1

HCID 706050833-(2-Morpholinoethoxy)-1-(3,4,5-trimethoxyphenylacetyl) pyrrolidine HemihydrateYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Under anhydrous conditions 5.3 g. crude 3,4,5-trimethoxyphenylacetic acid chloride [equivalent to 4.5 g. (0.0184 mole) by nuclear resonance spectrum analysis] in 20 ml. dry benzene was added dropwise to a stirring mixture of 3.7 g. (0.0184 mole) of 3-(2-morpholinoethoxy)pyrrolidine and 30 g. (0.0217 mole) of potassium carbonate in 50 ml. dry benzene. The product formed rapidly and separated out as a gummy mass. After stirring 1 hr. at room temperature, chloroform was stirred into the reaction mixture to dissolve the product. The inorganic materials were removed by filtration and the filtrate concentrated at reduced pressure to give 5.3 g. crude product (70% yield). A portion (2.6 g.) of the crude product was chromatographed on magnesium silicate to give 1.6 g. of pure product.

Workup

  1. customThe product formed rapidly
  2. customseparated out as a gummy mass
  3. stirringat room temperature, chloroform was stirred into the reaction mixture
  4. dissolutionto dissolve the product
  5. customThe inorganic materials were removed by filtration
  6. concentrationthe filtrate concentrated at reduced pressure
  7. customto give 5.3 g

Sources & evidence

ORD record
ord-384463053c1d43448333acbaf50ce46b
Source dataset
uspto-grants-1979_02
Patent number
US04139620

Reaction notes

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