HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide

HRID 1178032
Notes
Print preview

Reaction equation

HRID 1178032 reaction equation
CCN(C(C)C)C(C)C.[O:10]([C:17]1[CH:29]=[CH:28][C:20]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:51]([N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN(C=O)C.O>[CH2:51]([N:58]1[CH2:63][CH2:62][N:61]([C:25](=[O:27])[CH2:24][NH:23][C:21](=[O:22])[C:20]2[CH:19]=[CH:18][C:17]([O:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:29][CH:28]=2)[CH2:60][CH2:59]1)[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 81531DiisopropylethylamineHCID 24048312-[(4-Phenoxyphenyl)formamido]acetic acid

Product 1

HCID 27671405
N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide
Yield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.114 mL, 0.66 mmol) was added drop wise to (4-phenoxy-benzoylamino)-acetic acid (60 mg, 0.22 mmol) in DMF (5 mL). EDCI (106 mg, 0.55 mmol) and HOBT (35 mg, 0.27 mmol) were then added, and after 10 mins, 1-Benzyl-piperazine (46 mg, 0.27 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was added, and the resulting solid was isolated by filtration under reduced pressure to afford N-[2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-4-phenoxy-benzamide in 58% yield. LC-MS purity: 99%, 1H NMR (DMSO-D6): δ 8.5 (t, 1H), 7.9 (d, 2H), 7.5 (t, 2H), 7.3 (m, 7H), 7.1 (m, 4H), 4.1 (d, 2H), 3.6 (s, 2H), 3.5 (m, 4H), 2.4 (m, 4H).

Workup

  1. customthe resulting solid was isolated by filtration under reduced pressure

Sources & evidence

ORD record
ord-def73861ad794c1085fffa04b57b9c44
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842696B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes