Propargylamine → HCID 28419266, compound

HRID 597876Notes

Reaction equation

HRID 597876 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[CH2:11]([NH2:14])[C:12]#[CH:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][NH:14][CH2:11][C:12]#[CH:13]

Participants

6

Reactant 3

HCID 239041PropargylamineHCID 5880883,4-DifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28419266HCID 28419266, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3,4-difluorobenzaldehyde (5 g, 35.2 mmol) in 200 mL dichloroethane was added mono-propargyl amine (4.85 mL, 70.7 mmol, 2 eq.) followed by Na(OAc)3BH (9 g, 42.5 mmol) and the mixture was stirred for 2 days at room temperature. The solution was diluted with 100 mL of dichloromethane, washed with 2×100 mL aq. NaHCO3, 100 mL brine, dried over Na2SO4, filtered and concentrated. The crude product was chromatographed with 20:80 ethyl acetate-hexanes to provide 3.8 g of (3,4-difluoro-benzyl)-prop-2-ynyl-amine as an oil.

Workup

  1. washwashed with 2×100 mL aq. NaHCO3, 100 mL brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was chromatographed with 20:80 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-6367a64d04ff4b6dabf3078f62dcfede
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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