4-Amino-1-butanol → 4-(1,2-Benzisoxazol-3-ylamino)-1-butanol

HRID 275744Notes

Reaction equation

HRID 275744 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C(Cl)Cl.[I-].[K+]>[O:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[N:3]1

Participants

5

Reactant 2

HCID 258684-Amino-1-butanolHCID 27797803-Chloro-1,2-benzoxazole

Product 1

HCID 183789574-(1,2-Benzisoxazol-3-ylamino)-1-butanolYield 93.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-chloro-1,2-benzisoxazole (0.08 mol), 4-amino-1-butanol (0.24 mol) and potassium iodide (1 g) was stirred for 4 days at 80° C. The reaction mixture was cooled, dissolved in CH2Cl2 and purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 15.4 g (93%)of 4-(1,2-benzisoxazol-3-ylamino)-1-butanol (interm. 7). b) SOCl2 (0.048 mol) was cooled to 0° C. A solution of intermediate 7 (0.048 mol) in CHCl3 (20 ml) was added dropwise and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated. The residue was washed with water. The reaction mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered, and the solvent was evaporated, yielding 10.4 g of N-(4-chlorobutyl)-1,2-benzisoxazol-3-amine (interm. 8).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a37a3a890d5242feba69af330434052b
Source dataset
uspto-grants-2002_03
Patent number
US06352999B1

Reaction notes

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