1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86590387, compound

HRID 736361Notes

Reaction equation

HRID 736361 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12](C(OCC)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27](N)[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1.C[CH2:37][N:38]=[C:39]=NCCCN(C)C.C1C=CC2N([OH:56])N=NC=2C=1>CCN(CC)CC.C(Cl)Cl>[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:37][NH:38][C:39]([CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:56])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 109550394-Fluoro-alpha-(4-fluorophenyl)benzenemethanamineHCID 18997131HCID 18997131, compound

Product 1

HCID 86590387HCID 86590387, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-(phenylethyl)-4-(ethoxycarbonyl)piperidine (0.25 g, 0.95 mmol) was converted into its carboxylic acid, which was then reacted with bis(4-fluorophenyl)methyl amine (0.25 g, 1.14 mmol), EDCI (0.25 g, 1.27 mmol), HOBT (0.20 g, 1.48 mmol) in Et3N (1.5 ml) and CH2Cl2 (20 ml) to produce 4-[(bis(4-fluorophenyl)ethylamino)carbonyl-1-(phenylethyl)piperidine, 0.32 g (74% yield)(procedure E). 1H NMR (CD3Cl) δ 7.29-7.03 (10H, m, Ar—H), 7.05-6.99 (3H, m, Ar—H), 6.22-6.20 (1H, d, J=7.8 Hz), p-FPh2CH), 6.00-5.97 (1H, d, J=7.5 Hz, NH), 3.08-3.04 (2H, bd, J=11.4 Hz, N(CH)2), 2.83-2.78 (2H, d), 2.62-2.57 (2H, m), 2.25-2.15 (1H, m, NCOCH), 2.10-2.03 (2H, t, J=11.4 Hz, N(CH)2), 1.96-1.81 (4H, m).

Sources & evidence

ORD record
ord-011bc84b9b1a409d982380e4b191b455
Source dataset
uspto-grants-2009_09
Patent number
US07595331B2

Reaction notes

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