3-Amino-1-propanol → 2-[(3-hydroxypropyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide

HRID 434246Notes

Reaction equation

HRID 434246 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)=[O:4].[NH2:17][CH2:18][CH2:19][CH2:20][OH:21]>C(O)C>[OH:21][CH2:20][CH2:19][CH2:18][NH:17][CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 22487609N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-chloroacetamide

Product 1

HCID 224887192-[(3-hydroxypropyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-chloro-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide (0.45 g, 1.9 mmol) in ethanol (10 mL) was added 3-aminopropanol (0.72 mL, 9.4 mmol) (a compound of formula (Y9)). After heating the reaction in an oil bath at 60° C for 1 day, the reaction was partitioned with ethyl acetate and water. The organic layer was separated, washed with brine, dried (Na2SO4), and the solvent was removed in vacuo to give 0.44 g of 2-[(3-hydroxypropyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide, a compound of formula (Y10).

Workup

  1. temperatureAfter heating
  2. customthe reaction in an oil bath at 60° C for 1 day
  3. customthe reaction was partitioned with ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8886fab9e8c4427a9e3b68a29da394ec
Source dataset
uspto-grants-2003_12
Patent number
US06670473B2

Reaction notes

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