Acetyl chloride → HCID 70564247, compound

HRID 126914Notes

Reaction equation

HRID 126914 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([C@H:10]2[C@H:14]([OH:15])[CH2:13][N:12]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:11]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30](Cl)(=[O:32])[CH3:31]>O1CCOCC1.C(Cl)Cl>[OH2:7].[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([C@H:10]2[C@H:14]([OH:15])[CH2:13][N:12]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:11]2)[CH3:9])=[O:7])=[CH:22][CH:23]=1)(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 70565496HCID 70565496, compound

Product 1

HCID 70564247HCID 70564247, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 19 g. of trans-4-amino-N-(1-cyclohexyl-4-hydroxy-3-pyrrolidinyl)-N-methylbenzamide in 500 ml of p-dioxane was cooled to 10° and 30 g of powdered anhydrous potassium carbonate was added. The mixture was stirred and kept cool while 4.7 g of acetyl chloride in 50 ml of methylene chloride was added dropwise. The mixture was allowed to warm to room temperature and stirred for 24 hr. The mixture was filtered, the solvent was removed under vacuum and the residue was crystallized from aqueous acetone. Yield was 73%, m.p. 123°-127° C.

Workup

  1. additionwas added dropwise
  2. stirringstirred for 24 hr
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed under vacuum
  5. customthe residue was crystallized from aqueous acetone

Sources & evidence

ORD record
ord-f32adee00b5d49a9bfd49adf1603d1f9
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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