1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874413, compound

HRID 1093800Notes

Reaction equation

HRID 1093800 reaction equation
CCN(C(C)C)C(C)C.[N:10]1([C:15]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=2)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([O:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=2)[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[O:51]=[C:50]([N:52]1[CH2:53][CH2:54][CH:55]([O:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:66])[F:67])[CH:60]=2)[CH2:56][CH2:57]1)[CH2:49][NH:48][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[O:16])=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10932939Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-HCID 665915472-Amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride

Product 1

HCID 57874413HCID 57874413, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (200 mg, 1.5 mmol) was added to a stirred solution of 4-(pyrrolidine-1-carbonyl)-benzoic acid (75 g, 0.34 mmol) in DMF (5 mL) followed by HOBt (50 mg, 0.37 mmol) and EDCI (164 mg, 0.85 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (127 mg, 0.37 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected to afford 130 mg (75.58% Yield) of N-{2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-4-(pyrrolidine-1-carbonyl)-benzamide. LC/MS [M+H]+: 504, 94.9%. 1H NMR (300 MHz, DMSO-d6): δ 7.2 (t, 1H), 7.96 (d, 2H), 7.64-7.48 (m, 3H), 7.36 (t, 3H), 4.9 (b, 1H), 4.2 (d, 2H), 4.0 (d, 2H), 3.5 (t, 2H), 3.4 (t, 2H), 2.1-1.8 (m, 6H), 1.7 (m, 3H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customthe precipitate was collected

Sources & evidence

ORD record
ord-9989db17c5f24986b0f2141f6c259cce
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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