Hydrochloric Acid → N-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethyl pyrrolidine hydrochloride

HRID 35704Notes

Reaction equation

HRID 35704 reaction equation
[C:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.Cl>C(O)=O>[ClH:14].[Cl:15][C:10]1[CH:9]=[C:8]([C:4]2([CH:1]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH3:2])[CH2:7][CH2:6][CH2:5]2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

Product 1

HCID 13083311N-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethyl pyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-Acetyl-1-(3,4-dichlorophenyl)cyclobutane (7.0 g) prepared as described in Example 1 was slowly added to a mixture of pyrrolidine (25 ml) and 98% formic acid (15 ml) heated to 130°-135° C. for five hours. The mixture was stirred and heated at 160°-165° C. for sixteen hours. After cooling the mixture was poured into 5N hydrochloric acid (200 ml). The solution was washed with ether, basified with aqueous sodium hydroxide solution and extracted with ether. The ether extract was washed with water, dried and hydrogen chloride gas was passed into the extract which was then evaporated to dryness. The residue was triturated with dry ether to give a solid which was recrystallised from propan-2-ol to give N-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethyl pyrrolidine hydrochloride (m.p. 233°-235° C.) (Formula I R1 =Me; R2 =H; R3 and R4 together with the nitrogen to which they are attached form a pyrrolidine ring; R5 =4-- Cl and R6 =3--Cl).

Workup

  1. temperatureheated to 130°-135° C. for five hours
  2. temperatureheated at 160°-165° C. for sixteen hours
  3. temperatureAfter cooling the mixture
  4. washThe solution was washed with ether
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. customdried
  9. extractionextract which
  10. customwas then evaporated to dryness
  11. customThe residue was triturated with dry ether
  12. customto give a solid which
  13. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-c1db80e37e514b9d8b203d0c0c3d75e7
Source dataset
uspto-grants-1988_08
Patent number
US04767790

Reaction notes

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