Ammonia → HCID 22470546, compound

HRID 394984Notes

Reaction equation

HRID 394984 reaction equation
N.O.O[N:4]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([C:35]=1[CH2:36][CH2:37][CH2:38][C:39]1([C:54]([OH:56])=O)[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:41][CH2:40]1)=[CH:33][C:32]([O:57][CH3:58])=[CH:31][CH:30]=2.[Na]>O1CCOCC1.ClCCl.O.C(N(CC)CC)C>[Cl:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([C:35]=1[CH2:36][CH2:37][CH2:38][C:39]1([C:54]([NH2:4])=[O:56])[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:41][CH2:40]1)=[CH:33][C:32]([O:57][CH3:58])=[CH:31][CH:30]=2

Participants

10

Reactant 5

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5360545SodiumHCID 22398761HCID 22398761, compound

Product 1

HCID 22470546HCID 22470546, compoundYield 29.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

15.6 cm3 of a 0.5N solution of aqueous ammonia in dioxane, 0.26 g of 1-hydroxybenzotriazole hydrate, 0.75 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and 0.55 cm3 of triethylamine were added to a mixture of 0.75 g of 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxylic acid in the form of the sodium salt, in 20 cm3 of dichloromethane. The suspension obtained was stirred for 17 hours at a temperature in the region of 20° C. The reaction mixture was diluted with 25 cm3 of water and stirred, and the phases were then separated by settling. The aqueous phase was extracted with twice 25 cm3 of dichloromethane and the organic extracts were combined, washed with 25 cm3 of brine, dried over magnesium sulfate and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The evaporation residue obtained was purified by chromatography under a pressure of 50 kPa of argon, on a column of silica gel (particle size 20-45μ; diameter 3 cm; height 21 cm), eluting with a mixture of dichloromethane/methanol (90/10 by volume). The fractions containing the product were combined and then concentrated to dryness under the above conditions. 0.22 g of 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-4-carboxamide was obtained in the form of a white solid melting at 160° C.

Workup

  1. customThe suspension obtained
  2. stirringstirred
  3. customthe phases were then separated
  4. extractionThe aqueous phase was extracted with twice 25 cm3 of dichloromethane
  5. washwashed with 25 cm3 of brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  8. customThe evaporation residue obtained
  9. customwas purified by chromatography under a pressure of 50 kPa of argon, on a column of silica gel (particle size 20-45μ; diameter 3 cm; height 21 cm)
  10. washeluting with a mixture of dichloromethane/methanol (90/10 by volume)
  11. additionThe fractions containing the product
  12. concentrationconcentrated to dryness under the above conditions

Sources & evidence

ORD record
ord-08498de6113e47a2851ae83a6162d64d
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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