Triethylamine → HCID 57842797, compound

HRID 735599Notes

Reaction equation

HRID 735599 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[C:4]([CH2:11][CH3:12])[CH:3]=1.C[CH2:14][N:15](CC)CC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:15][CH3:14])=[C:4]([CH2:11][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 578427842-(4-Bromo-2-ethylphenyl)ethanol

Product 1

HCID 57842797HCID 57842797, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mesyl anhydride (430 mg, 2.46 mmol) was added portionwise to a solution of 36B (470 mg, 2.05 mmol) in CH2Cl2 (10 mL) and Et3N (0.57 mL, 4.1 mmol) at 0° C. After stirring for 15 h at ambient temperature, the mixture was diluted with CH2Cl2 (80 mL), washed with 1.0 M HCl, NaHCO3, brine, dried over Na2SO4 and concentrated in vacuo. The crude mesylate was dissolved in EtOAc (20 mL) and methyl amine (33%, 5 mL) and heated in a pressure tube for 2 h. The reaction mixture was concentrated in vacuo to afford 36C (500 mg, 99%) as a yellow oil. MS (ESI) m/z 242.0/244.0 (M+H)+.

Workup

  1. washwashed with 1.0 M HCl, NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude mesylate was dissolved in EtOAc (20 mL)
  5. temperaturemethyl amine (33%, 5 mL) and heated in a pressure tube for 2 h
  6. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-868f5152227a4bb884f168c777f52438
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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