Potassium Hydroxide → 1-(3-Chloropropyl)-pyrrolidine

HRID 407276Notes

Reaction equation

HRID 407276 reaction equation
C(O)(=O)C(O)=O.[Cl:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(OC)(C)(C)C.[OH-].[K+]>O>[Cl:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 15413tert-Butyl methyl etherHCID 248970761-(3-Chloropropyl)pyrrolidine oxalate

Product 1

HCID 113210281-(3-Chloropropyl)-pyrrolidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(3-Chloropropyl)pyrrolidine oxalate (134.8 kg) was suspended in water (226 l) and methyl tert-butyl ether (83.4 kg) added. The stirred mixture was basified to pH>11 by addition of 49% w/w aqueous potassium hydroxide solution (138.9 kg). A line wash of water (22.6 l) was applied. The lower aqueous layer was separated and transferred to a second reactor. The upper organic layer was transferred to 200 l drums. A line wash of methyl tert-butyl ether (16.7 kg) was applied. The aqueous layer was recharged to the original reactor and further extracted with methyl tert-butyl ether (83.4 kg). The lower aqueous layer was discarded. The original organic layer was recharged from the drums. A line wash of methyl tert-butyl ether (16.7 kg) was applied. The combined organic layers were washed with 23% w/w aqueous potassium chloride solution (64.8 kg) to give a solution of 1-(3-chloropropyl)pyrrolidine (83.9 kg) in methyl tert-butyl ether. The required amount of solution can then be used as appropriate.

Workup

  1. washA line wash of water (22.6 l)
  2. customThe lower aqueous layer was separated
  3. customtransferred to a second reactor
  4. washA line wash of methyl tert-butyl ether (16.7 kg)
  5. extractionfurther extracted with methyl tert-butyl ether (83.4 kg)
  6. washA line wash of methyl tert-butyl ether (16.7 kg)
  7. washThe combined organic layers were washed with 23% w/w aqueous potassium chloride solution (64.8 kg)

Sources & evidence

ORD record
ord-52322dd211c44074a5f1c83756afdd8b
Source dataset
uspto-grants-2014_06
Patent number
US08754240B2

Reaction notes

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