Pyridine → Methyl 3-(2-Chloropropanamido)propanoate

HRID 215908Notes

Reaction equation

HRID 215908 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:15])[CH2:12][CH2:13][NH2:14].N1C=CC=CC=1.[Cl:22][CH:23]([CH3:27])[C:24](Cl)=[O:25]>ClCCl>[CH3:9][O:10][C:11](=[O:15])[CH2:12][CH2:13][NH:14][C:24](=[O:25])[CH:23]([Cl:22])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 43665913Methyl 3-(2-Chloropropanamido)propanoateYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.63 g) was added to a suspension of β-alanine methyl ester hydrochloride (2.25 g) in dichloromethane (10 mL) and the reaction mixture was stirred for 30 minutes. After addition of pyridine (1.27 g) the reaction mixture was cooled to 0° C. A solution of 2-chloropropionyl chloride (2.04 g) in dichloromethane (10 mL) was added dropwise for 20 minutes. The reaction mixture was stirred for 2 hours, washed sequentially with water, 1 N hydrochloric acid and saturated sodium bicarbonate, dried with magnesium sulfate, filtered, and concentrated to give yellow oil (2.9 g, yield 93%).

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. washwashed sequentially with water, 1 N hydrochloric acid and saturated sodium bicarbonate
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-205044f7b146465e85e1646f1f02c17f
Source dataset
uspto-grants-2012_06
Patent number
US08193198B2

Reaction notes

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