Acetyl chloride → HCID 14306823, compound

HRID 1682023Notes

Reaction equation

HRID 1682023 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][N:17]3[CH2:25][C:24]4[C:19](=[CH:20][C:21]([O:28][CH3:29])=[C:22]([O:26][CH3:27])[CH:23]=4)[C:18]3=[O:30])[CH2:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C(Cl)Cl>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][N:17]3[CH2:25][C:24]4[C:19](=[CH:20][C:21]([O:28][CH3:29])=[C:22]([O:26][CH3:27])[CH:23]=4)[C:18]3=[O:30])[CH2:11]2)=[CH:6][CH:7]=1)[C:38]([CH3:39])=[O:40]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14306822HCID 14306822, compound

Product 1

HCID 14306823HCID 14306823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

819 mg (2 mmol) of 2-[(N-(2-(4-amino-phenyl)-ethyl)-piperidin-3-yl)-methyl]-5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole are mixed with 10 ml of methylene chloride and after the addition of 0.3 ml (2.2 mmol) of triethylamine, 0.16 ml (2.2 mmol) of acetyl chloride are added dropwise. The reaction temperature rises to 30° C. The mixture is stirred for half an hour at ambient temperature, extracted twice with water, the organic phase is dried over magnesium sulphate and evaporated down in vacuo. The residue is crystallised from acetone.

Workup

  1. additionare added dropwise
  2. customrises to 30° C
  3. extractionextracted twice with water
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. customevaporated down in vacuo
  6. customThe residue is crystallised from acetone

Sources & evidence

ORD record
ord-d099f20decfc4638a325eba9c2479bf3
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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