Water → HCID 43390057, compound

HRID 1190181Notes

Reaction equation

HRID 1190181 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](Cl)=[O:24])=[CH:18][CH:17]=1)([O-:15])=[O:14].O>C(Cl)Cl>[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:23](=[O:24])[CH2:22][C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 6452210Benzeneacetyl chloride, 4-nitro-

Product 1

HCID 43390057HCID 43390057, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-hydroxypropylamine (507 mg, 6.76 mmol) and triethylamine (1.88 mL, 0.013 mol) in DCM (10 mL) at 0° C. was added (4-nitro-phenyl)-acetyl chloride (1.35 g, 6.76 mmol) in DCM (10 mL) dropwise. The dark red solution was allowed to warm to room temperature and then poured into water (50 mL). The layers were separated and the organic layer was dried (Na2SO4) and concentrated in vacuo. The crude material was purified by preparative thin layer chromatography (TLC) (5%-MeOH—CHCl3) to afford 183 mg (11%) of the title compound as a solid. 1H-NMR (CDCl3; 400 MHz): δ 8.12 (d, 2H, J=8.7 Hz), 7.39 (d, 1H, J=8.7 Hz), 6.09 (br s, 1H), 3.58 (s, 2H), 3.57-3.54 (m, 2H), 3.40 (br s, 1H), 3.36-3.31 (m, 2H), 1.63-1.57 (m, 2H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by preparative thin layer chromatography (TLC) (5%-MeOH—CHCl3)

Sources & evidence

ORD record
ord-833ff3194e7f4aeaafc7f93bd23daa38
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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