Pyridine → HCID 21475970, compound

HRID 2293411Notes

Reaction equation

HRID 2293411 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20]>ClCCl>[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1)([O:21][CH2:22][CH:23]=[CH2:24])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 2204244-Aminobenzenepropanol

Product 1

HCID 21475970HCID 21475970, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask was added the 3-(4-aminophenyl)propanol (1.3 g, 8.6 mmol), pyridine (1.0 mL, 12 mmol) and dichloromethane (25 mL). The solution was cooled to 0° C. and treated with allyl chloroformate (1.0 mL, 9.4 mmol). After allowing to warm to 22° C. over 1 hour, the reaction mixture was diluted with dichloromethane and washed twice with 1N HCl, followed by sat. NaHCO3, water and sat. aq. NaCl. The organic extract was dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (50% EtOAc in hexane), provided 1.77 g (88%) of 3-(4-(N-carboallyloxy)aminophenyl)propanol as a clear oil which solidified on standing.

Workup

  1. temperatureto warm to 22° C. over 1 hour
  2. washwashed twice with 1N HCl
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-f0bb024aa09d46e3be24aefc6e9da71a
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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