Acryloyl chloride → ACRYLAMIDO BUFFER

HRID 1615282Notes

Reaction equation

HRID 1615282 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:17](=[O:20])[CH:18]=[CH2:19])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 13742939ACRYLAMIDO BUFFER

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A dry round-bottom flask was charged with 1-methylpiperazine (0.15 mL, 1.36 mmol), diisopropylethylamine (0.65 mL, 3.72 mmol) and CH2Cl2 (6 mL) and then the solution was cooled with an ice-water bath. Acryloyl chloride (0.10 mL, 1.24 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. After 3 hours TLC indicated reaction completion. The CH2Cl2 was removed and the residue taken up in EtOAc, washed with NaHCO3 (sat.) (1×), brine (2×) and then dried over MgSO4. The EtOAc was removed in vacuo which yielded after drying, the title compound as an orange-brown oil. (400 MHz, CDCl3) 6.57 (dd, J1=16.8 Hz, J2=10.5 Hz, 1H), 6.29 (d, J=16.8 Hz, 1H), 5.70 (d, J=10.5 Hz, 1H), 3.73 (bs, 2H), 3.60 (bs, 2H), 2.46-2.41 (m, 4H), 2.34 (s, 3H); MS ESI 155.0 [M+H]+, calcd for [C8H14N2O+H]+

Workup

  1. temperaturethe solution was cooled with an ice-water bath
  2. customAfter 3 hours TLC indicated reaction completion
  3. customThe CH2Cl2 was removed
  4. washwashed with NaHCO3 (sat.) (1×), brine (2×)
  5. dry with materialdried over MgSO4
  6. customThe EtOAc was removed in vacuo which
  7. customyielded
  8. customafter drying

Sources & evidence

ORD record
ord-a07692a3b48a46cf9854e58d4a7333e1
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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