1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 16755969, compound

HRID 1269156Notes

Reaction equation

HRID 1269156 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:29]=[C:30]([NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[CH:31]=[CH:32][CH:33]=2)[CH2:24][CH2:23]1.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C=O)C>[C:35]([NH:34][C:30]1[CH:29]=[C:28]([CH:25]2[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][NH:18][C:8](=[O:10])[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:11])[CH2:23][CH2:24]2)[CH:33]=[CH:32][CH:31]=1)(=[O:39])[CH:36]([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 796762,2-Diphenylpropionic acidHCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamide

Product 1

HCID 16755969HCID 16755969, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A mixture of 2,2-diphenylpropionic acid (0.200 mmol, 45.2 mg), N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide (0.200 mmol, 60.7 mg), 1-[3-(dimethylamino)propyl]3-ethylcarbodiimide (EDC, 0.400 mmol, 62.0 mg) and 4-dimethylaminopyridine (5.00 mg) was dissolved in CH2Cl2/DMF (1.00/0.100 mL) and the mixture was shaken on an orbital J-KEM shaker at room temperature for 12 h. The reaction mixture was concentrated in vacuo, purified by preparative TLC [silica, CH2Cl2:ammonia (2.0 M in methanol) 100:5] to afford the desired product (43.8 mg, 42% yield): 1H NMR (400 MHz, CDCl3) δ 7.50–7.43 (br, 1H), 7.43–7.39 (br, 1H), 7.39–7.18 (m, 12H), 6.89 (d, 1H, J=7.7 Hz), 6.23 (br, 1H) 3.42–3.32 (m, 2H), 2.85 (d, 2H, J=10.8 Hz), 2.50 (quintet, 1H, J=7.4 Hz), 2.45–2.36 (m, 1H), 2.28 (t, 2H, J=6.4 Hz), 1.99 (s, 3H), 1.96–1.82 (m, 2H), 1.78–1.60 (m, 4H), 1.60–1.47 (m, 2H), 1.23 (d, 6H, J=7.0 Hz); ESMS m/e: 512.4 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by preparative TLC [silica, CH2Cl2:ammonia (2.0 M in methanol) 100:5]

Sources & evidence

ORD record
ord-61d1b30321ac4bf6b23cf9e9366c1a1b
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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