Diisopropylethylamine → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trifluoro-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide

HRID 265977Notes

Reaction equation

HRID 265977 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:14][CH2:15]O)[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([F:28])[C:26]=1[F:27])[C:21]([OH:23])=O.C([N:32]([CH2:36][CH3:37])[CH:33]([CH3:35])C)(C)C.Cl.C(N=C=N[CH2:44][CH2:45][CH2:46][N:47](C)C)C.[OH2:50].ON1[C:56]2[CH:57]=C[CH:59]=[CH:60][C:55]=2N=N1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:14][CH2:15][N:32]3[CH2:33][CH2:35][C:45]([C:44]4[CH:59]=[CH:60][CH:55]=[CH:56][CH:57]=4)([C:46]([NH2:47])=[O:50])[CH2:37][CH2:36]3)[CH2:13][CH2:12][N:11]([C:21](=[O:23])[C:20]3[CH:24]=[C:25]([F:28])[C:26]([F:27])=[C:18]([F:17])[CH:19]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 8531543,4,5-Trifluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanol

Product 1

HCID 544965181-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trifluoro-benzoyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 3-(3,4-dichloro-phenyl)-3-(2-hydroxy-ethyl)-pyrrolidine (286 mg, 1.1 mmol), 3,4,5-trifluoro-benzoic acid (1 mmol), N,N-diisopropylethylamine (0.19 mL, 1.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) (0.21 g, 1.1 mmol), and 1-hydroxybenzotriazole hydrate (HOBT) (0.15 g, 1.1 mmol) in dichloromethane (10 mL). After 18 hour, dilute with dichloromethane and extract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound: Rf =0.45 (silica gel, 10% methanol/dichloromethane).

Workup

  1. extractionextract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-f338b91f5520421085dc3859a38be1e0
Source dataset
uspto-grants-1997_07
Patent number
US05648366

Reaction notes

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