Triethylamine → HCID 69082365, compound

HRID 2059729Notes

Reaction equation

HRID 2059729 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.CCN(CC)CC.Cl[C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC#N>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 123460Methyl malonyl chlorideHCID 27240964-Bromobenzylamine hydrochloride

Product 1

HCID 69082365HCID 69082365, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-(4-bromophenyl)methanamine hydrochloride (8.56 g, 38.5 mmol), MeCN (50 mL) and NEt3 (5.36 mL, 38.5 mmol) was added methyl 3-chloro-3-oxopropanoate (3.17 mL, 29.6 mmol). The reaction was aged about an hour before NEt3 (10.7 mL, 77 mmol) was added. The reaction was aged about 20 min and was concentrated. The reaction was diluted with EtOAc and washed with brine and aq. 2M Na2CO3 solution followed by aq. 2 M HCl and water. The organic portion was concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-90% EtOAc/hexane to afford the product.

Workup

  1. additionwas added
  2. concentrationwas concentrated
  3. additionThe reaction was diluted with EtOAc
  4. washwashed with brine and aq. 2M Na2CO3 solution
  5. concentrationThe organic portion was concentrated
  6. customThe residue was purified by flash chromatography on silica gel gradient
  7. washeluted with 0-90% EtOAc/hexane
  8. customto afford the product

Sources & evidence

ORD record
ord-828c7c93f4f448a7b966dda49126dfef
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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