Diisopropylethylamine → 3-chloro-N-(2-morpholin-4-ylethyl)-4-nitro-benzamide

HRID 2234371Notes

Reaction equation

HRID 2234371 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](Cl)=[O:6].C(N(CC)C(C)C)(C)C.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 190776143-Chloro-4-nitrobenzoyl chloride2×

Product 1

HCID 686820563-chloro-N-(2-morpholin-4-ylethyl)-4-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-chloro-4-nitro-benzoyl chloride (Intermediate 54; 1.1 g, 5.00 mmol) was dissolved in DCM (10 mL) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol) added. The mixture was cooled in an ice/water bath and 4-(2-aminoethyl)morpholine (Aldrich; 0.66 mL, 5.00 mmol) in DCM (5 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 hr. The reaction mixture was washed with brine, 2N NaOH, dried (MgSO4) and concentrated. Column chromatography of the residue (2% MeoH/DCM) gave the title compound as a yellow solid. (1.2 g, 76%)

Workup

  1. temperatureThe mixture was cooled in an ice/water bath
  2. washThe reaction mixture was washed with brine, 2N NaOH
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f315437d9a14764a797a75efcb37da4
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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