Water → HCID 70563141, compound

HRID 126919Notes

Reaction equation

HRID 126919 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+].[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18].O>C(Cl)Cl>[CH2:1]([N:3]1[CH2:4][C@@H:5]([OH:10])[C@H:6]([N:8]([CH3:9])[C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[CH2:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium CarbonateHCID 70565576HCID 70565576, compound

Product 1

HCID 70563141HCID 70563141, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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°. The mixture was kept at or below 0° C. while a solution of 22.0 g (118 mmoles) of p-nitrobenzoyl 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 benzene to give 30 g (87%) of white crytals; m.p. 104°-108° C.

Workup

  1. temperaturecooled to -5°
  2. custombelow 0° C.
  3. additionwas added dropwise
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from benzene
  8. customto give 30 g (87%) of white crytals

Sources & evidence

ORD record
ord-1d1f4c8940ba475294fb05d7e1eb54ac
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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