1,2-Dichloroethane → HCID 49372722, compound

HRID 1511874Notes

Reaction equation

HRID 1511874 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([NH2:18])[C:16]#[CH:17].C(N(C(C)C)CC)(C)C.OC1C2N=NNC=2C=CC=1.C(Cl)CCl>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:18][CH2:15][C:16]#[CH:17])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 5622014-(Benzyloxy)butanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 49372722HCID 49372722, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-Benzyloxy-butyric acid (1.00 g, 5.15 mmol) and Propargylamine (284 mg, 5.15 mmol) in DMF (10.3 ml) was treated with Diisopropylethylamine (0.90 ml, 5.15 mmol), Hydroxybenzotriazole (788 mg, 5.15 mmol) and EDC (665 mg, 5.15 mmol) at room temperature. The resulting mixture was stirred overnight at room temperature under nitrogen. The reaction was concentrated under reduced pressure and the crude product is taken up in Ethyl acetate, washed with water, dried using Na2SO4, filtered, and concentrated to yield 4-Benzyloxy-N-prop-2-ynyl-butyramide (1.02 g, 86%) as a viscous oil.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9435242a21f24d84bf9c201b9f43db55
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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