Triethylamine → HCID 54757545, compound

HRID 500604Notes

Reaction equation

HRID 500604 reaction equation
O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:19]([C:21]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][CH2:23][C:24](O)=[O:25])#[N:20].Cl.[O:40]([CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[O:25]=[C:24]([N:50]1[CH2:51][CH2:52][CH:47]([O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:48][CH2:49]1)[CH2:23][CH2:22][C:21]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:19]#[N:20]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 177497864-Phenoxypiperidine--hydrogen chloride (1/1)HCID 537742904-Cyano-4,4-diphenylbutanoic acid

Product 1

HCID 54757545HCID 54757545, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole hydrate (5.67 g, 42 mmol) and triethylamine (14.88 mL, 107 mmol) were added to 4-cyano-4,4-diphenylbutanoic acid (WO97/24325) (10.39 g, 39 mmol) and 4-phenoxy-piperidine hydrochloride (6.32 g, 36 mmol) in N,N-dimethylformamide (150 mL). The mixture was stirred for 10 minutes. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.20 g, 42 mmol) was then added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, washed with water (100 mL) and brine (30 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether, filtered off, washed through with diethyl ether and purified by column chromatography on silica gel, eluting with pentane:ethyl acetate, 75:25 to 50:50, to afford the title compound as a white solid (14.4 g) in a 95% yield.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. washwashed with water (100 mL) and brine (30 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with diethyl ether
  9. filtrationfiltered off
  10. washwashed through with diethyl ether
  11. custompurified by column chromatography on silica gel
  12. washeluting with pentane

Sources & evidence

ORD record
ord-1794ddb344dd40d2bf5add2e7dc97234
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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