1-(3-Aminophenyl)ethanol → HCID 15670991, compound

HRID 2259967Notes

Reaction equation

HRID 2259967 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:16][C:17]([N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])[C:10](=[O:15])[CH2:11][N:12]=[C:13]=[O:14])[CH:6]=[CH:7][CH:8]=1.[OH:27][CH:28]([C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33])[CH3:29]>O1CCCC1>[OH:27][CH:28]([C:30]1[CH:31]=[C:32]([NH:33][C:13](=[O:14])[NH:12][CH2:11][C:10]([N:9]([CH2:16][C:17]([N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:15])[CH:34]=[CH:35][CH:36]=1)[CH3:29]

Participants

4

Reactant 2

HCID 2224611-(3-Aminophenyl)ethanolHCID 15670983HCID 15670983, compound

Product 1

HCID 15670991HCID 15670991, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

2-[N-(3-Methoxyphenyl)isocyanatoacetamido]-N-methyl-N-phenylacetamide (3 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of 3-(1-hydroxyethyl)aniline (1.1 g) in anhydrous tetrahydrofuran (20 cc). The solution obtained is stirred for 16 hours at a temperature in the region of 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residual oil is purified by chromatography on silica (0.063-0.2 mm) (150 g) contained in a column 2.5 cm in diameter) [eluent: dichloromethane/methanol (98:2 by volume)], collecting 20-cc fractions. The fractions containing only the desired product are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallisation in diisopropyl ether, (RS)-2-[2-{3-[3-(1-hydroxyethyl)phenyl]ureido}-N-(3-methoxyphenyl)acetamido]-N-methyl-N-phenylacetamide (1.7 g), m.p. 115° C., is thereby obtained.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  3. customThe residual oil is purified by chromatography on silica (0.063-0.2 mm) (150 g)
  4. customcollecting 20-cc fractions
  5. additionThe fractions containing only the desired product
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. customAfter recrystallisation in diisopropyl ether

Sources & evidence

ORD record
ord-47937d2b98594530a1eeccdc89281d80
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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