Water → HCID 70565610, compound

HRID 126917Notes

Reaction equation

HRID 126917 reaction equation
[CH2:1]([N:3]1[CH2:7][C@@H:6]([NH:8][CH3:9])[C@H:5]([OH:10])[CH2:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.O>C(Cl)Cl>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:8]([C@H:6]2[C@H:5]([OH:10])[CH2:4][N:3]([CH2:1][CH3:2])[CH2:7]2)[CH3:9])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 70565576HCID 70565576, compound

Product 1

HCID 70565610HCID 70565610, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 17.0 g (118 mmoles) of trans-1-ethyl-4-methylamino-3-pyrrolidinol in 180 ml of methylene chloride was mixed with 15 g of powdered anhydrous potassium carbonate and cooled to -5° C. The mixture was kept at or below 0° C. while a solution of 20.6 g (118 mmoles) of p-chlorobenzoyl chloride in 100 ml of methylene chloride was added dropwise. After the mixture was stirred at ambient temperature for 18 hr, it was poured into 100 ml of water. The organic layer was separated, dried and concentrated. The residue was crystallized from cyclohexane to give 25 g (75%) of white crystals, m.p. 91°-93° C.

Workup

  1. custombelow 0° C.
  2. additionwas added dropwise
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from cyclohexane

Sources & evidence

ORD record
ord-2615544ee2914f0e8b0e5e38abb92c7c
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

Loading…