Pyrrolidine → HCID 54431384, compound

HRID 2165408Notes

Reaction equation

HRID 2165408 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:27])=[N:5][O:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][CH2:24][CH2:25][N:26]=2)=[CH:18][CH:17]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C)C=O>[O:23]1[CH2:24][CH2:25][N:26]=[C:22]1[C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]2[O:6][N:5]=[C:4]([CH3:27])[C:3]=2[CH2:2][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 20063978HCID 20063978, compound

Product 1

HCID 54431384HCID 54431384, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.8 g of 4-chloromethyl-5-{7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole (Example 35) and 1.3 g of pyrrolidine in 50 ml of dimethylformamide was heated on a steam bath for six hours and then kept overnight at room temperature. The solvent was removed in vacuo, and the residue was dissolved in water and made basic with sodium bicarbonate solution. The solid product which separated was collected and dried to give 1.3 g of 5-{7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl}-3-methyl-4-(1-pyrrolidylmethyl)isoxazole, m.p. 98°-99° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. customThe solid product which separated
  4. customwas collected
  5. customdried

Sources & evidence

ORD record
ord-56b0b4cf5fba453293bb9df95cecf2a7
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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