Dicyclohexylcarbodiimide → HCID 10087040, compound

HRID 1898973Notes

Reaction equation

HRID 1898973 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH3:9].[Cl:10][C:11]1[CH:12]=[C:13]([CH2:18][C:19](O)=[O:20])[CH:14]=[CH:15][C:16]=1[Cl:17].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([CH2:18][C:19]([NH:1][CH2:2][CH:3]2[CH2:7][CH2:6][CH2:5][N:4]2[CH2:8][CH3:9])=[O:20])[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 798743,4-Dichlorophenylacetic acidHCID 1172952-Aminomethyl-1-ethylpyrrolidine

Product 1

HCID 10087040HCID 10087040, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Aminomethyl-1-(ethyl)pyrrolidine (Aldrich) (3.2 g, 25 mmol) and 3,4-dichlorophenylacetic acid (7.7 g, 37.6 mmol, 1.5 eq) were coupled in CH2Cl2 in the presence of DCC (10.6 g, 51 mmol, 2 eq) as described in Example 7 to give the desired product (7.6 g, 97%) as a colorless oil: 1H-NMR (CDCl3) ∂7.41 (d, J=8.2 Hz, 1H), 7.39 (d, J=2.0 Hz, 1H), 7.13 (dd, J=2.0, 8.2 Hz, 1H), 6.13 (br s, 1H), 3.51 (s, 2H), 3.37 (m, 1H), 3.07 (m, 2H), 2.65 (m, 1H), 2.53 (m, 1H), 2.04-2.21 (m, 2H, CH2CH3 ), 1.81 (m, 1H), 1.67 (m, 1H), 1.35-1.60 (complex m, 2H), 0.99 (t, J=7.2 Hz, 3H); CIMS (MH+ calcd for C15H20Cl2N2O): 315. Found (MH+): 315; Anal. (calcd for C15H20Cl2N2O): C,H,N.

Sources & evidence

ORD record
ord-1c540bb44c8a4673b33659062a3e84ce
Source dataset
uspto-grants-1996_11
Patent number
US05571832

Reaction notes

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