3-Amino-1-propanol → HCID 10799880, compound

HRID 989281Notes

Reaction equation

HRID 989281 reaction equation
Br[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([OH:13])=[CH:8][CH:9]=2)[O:4]1.[NH2:14][CH2:15][CH2:16][CH2:17][OH:18]>O>[OH:13][C:7]1[CH:6]=[C:5]2[C:10]([CH2:11][CH2:12][CH:3]([CH2:2][NH:14][CH2:15][CH2:16][CH2:17][OH:18])[O:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 18005873HCID 18005873, compound

Product 1

HCID 10799880HCID 10799880, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromomethyl-7-hydroxychroman (4.57 g, 18.8 mmol) and 3-amino-1-propanol (18.3 mL, 240 mmol) is heated at 100° C. for 2 hr, cooled, diluted with water and extracted with CH2Cl2. The combined extracts are concentrated in vacuo to give a residue. The residue is purified by column chromatography (silica gel/5% methanol in CH2Cl2 as eluent) to give the title product as a clear oil, 3.27 g (73% yield) identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled
  2. extractionextracted with CH2Cl2
  3. concentrationThe combined extracts are concentrated in vacuo
  4. customto give a residue
  5. customThe residue is purified by column chromatography (silica gel/5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-ea8256ac10da492b8aa54fa19e6b6a36
Source dataset
uspto-grants-2003_10
Patent number
US06638972B2

Reaction notes

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