Ethanolamine → HCID 4719060, compound

HRID 1779031Notes

Reaction equation

HRID 1779031 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].CCN(C(C)C)C(C)C.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15]>C(Cl)Cl>[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:4][CH2:3][CH2:1][OH:2])=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 660114-Nitrobenzyl bromideHCID 81531Diisopropylethylamine

Product 1

HCID 4719060HCID 4719060, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethanolamine (10.05 mL, 166.6 mmol), DIPEA (5.08 mL, 29.2 mmol) and 4-nitrobenzyl bromide (6.00 g, 27.8 mmol) in DCM (50 mL) was stirred at room temperature for 4 hours. The volatiles were removed in vacuo and the resulting residue partitioned between water and EtOAc. The aqueous phase was separated and extracted with EtOAc (3×30 mL). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound A68 as a light yellow solid (3.34 g, 61%); 1H NMR (300 MHz, d6-DMSO) δ 8.18 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H), 4.49 (t, J=5.4 Hz, 1H), 3.84 (s, 2H), 3.47 (q, J=5.6 Hz, 2H), 2.56 (t, J=5.8 Hz, 2H), 2.28 (s, 1H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between water and EtOAc
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc (3×30 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a13dd2eecfd24b119bb1533639527945
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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