Acetyl chloride → HCID 67032412, compound

HRID 920563Notes

Reaction equation

HRID 920563 reaction equation
C([Cl:4])(=O)C.C(OC([N:12]1[CH2:17][CH2:16][O:15][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:33])=[CH:20][CH:19]=2)[CH2:13]1)=O)(C)(C)C>C(O)C>[ClH:4].[Cl:32][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:33])[C:26]=1[CH2:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([CH:14]2[O:15][CH2:16][CH2:17][NH:12][CH2:13]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67032756HCID 67032756, compound

Product 1

HCID 67032412HCID 67032412, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Acetyl chloride (1.35 mL, 8.9 mmol) was added to ethanol (60 mL). The resulting solution was added to 2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (1.54 g; 3.4 mmol), at RT. The resulting mixture was stirred at 60° C. for 3 hours, and subsequently, at RT for three days. The resulting suspension was concentrated in vacuo, and treated with iPr2O. The formed precipitate was collected by filtration and dried in vacuo to afford 2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine hydrochloride (1.31 g).

Workup

  1. waitsubsequently, at RT for three days
  2. concentrationThe resulting suspension was concentrated in vacuo
  3. additiontreated with iPr2O
  4. filtrationThe formed precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8a600427788049999251ab4065dd8b59
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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