2-Chloroquinoline-4-carbonyl chloride → N-Methyl-N-(1-cyclohexyl-3-pyrrolidinyl)-2-chloro-4-quinolinecarboxamide Hydrochloride

HRID 371615Notes

Reaction equation

HRID 371615 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([NH:12][CH3:13])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:24]=[C:23]([C:25](Cl)=[O:26])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>C1C=CC=CC=1>[ClH:14].[CH3:13][N:12]([CH:9]1[CH2:10][CH2:11][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8]1)[C:25]([C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([Cl:14])[CH:24]=1)=[O:26]

Participants

4

Reactant 2

HCID 754382-Chloroquinoline-4-carbonyl chlorideHCID 128957171-Cyclohexyl-N-methylpyrrolidin-3-amine

Product 1

HCID 20355402N-Methyl-N-(1-cyclohexyl-3-pyrrolidinyl)-2-chloro-4-quinolinecarboxamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 12.7 g. (0.07 mole) of 1-cyclohexyl-3-methylaminopyrrolidine in dry benzene was added dropwise with stirring 15 g. (0.07 mole) of 2-chloroquinoline-4-carbonyl chloride in dry benzene. After 0.5 hr. the solution was extracted with dilute hydrochloric acid and the acidic solution made basic with sodium hydroxide solution and extracted with benzene. The benzene extracts were dried over sodium sulfate and concentrated. The residue was chromatographed on an aluminum silicate column eluting with a mixture of acetone benzene progressing from pure benzene to 50% acetone-benzene. The fractions containing the desired product were concentrated and the residue crystallized as the hydrochloride salt from isopropyl ether. The salt was recrystallized from isobutyl methyl ketone. Yield 10 g. (36%); m.p. 230°-233° C.

Workup

  1. extractionthe solution was extracted with dilute hydrochloric acid
  2. extractionextracted with benzene
  3. dry with materialThe benzene extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on an aluminum silicate column
  6. washeluting with a mixture of acetone benzene progressing from pure benzene to 50% acetone-benzene
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated
  9. customthe residue crystallized as the hydrochloride salt from isopropyl ether
  10. customThe salt was recrystallized from isobutyl methyl ketone

Sources & evidence

ORD record
ord-acfa671600c040e4afb577be5018db5c
Source dataset
uspto-grants-1978_05
Patent number
US04087428

Reaction notes

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