1-Phenethylamine → HCID 11792457, compound

HRID 736362Notes

Reaction equation

HRID 736362 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18]CC)=O)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:21]1([CH:27]([NH2:29])[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(C(O)=O)(F)(F)F.Cl.O.C(Cl)Cl>[C:21]1([CH:27]([NH:29][C:16]([CH2:15][CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:14][CH2:13]2)=[O:18])[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 74081-PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10779058HCID 10779058, compound

Product 1

HCID 11792457HCID 11792457, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 88143523HCID 88143523, compoundSolvent

Procedure

1-[(4-fluorophenyl)methyl]-4-[(ethoxycarbonyl)methyl]piperidine (0.55 g, 1.97 mmol) was refluxed in CF3CO2H/HCl/H2O (1:1:1) 10 ml to give the corresponding acid, which was then reacted with 1-phenylethylamine (0.29 g, 2.40 mmol), EDCI (0.56 g, 2.97 mmol) and HOBT (0.40 g, 2.96 mmol) in CH2Cl2 (10 ml) to produce a solid, 0.33 g (50% yield)(procedure D). 1H NMR (CD3Cl) δ 7.35-7.23 (7H, m, Ar—H), 7.00-6.94 (2H, t, J=8.4 Hz, Ar—H), 5.83-5.80 (1H, bd, J=7.5 Hz, NH), 5.15-5.10 (m, 1H, PhCHMe), 3.42 (s, 2H, p-PhCH2N), 2.83-2.78 (m, 2H, N(CH)2), 2.07-2.05 (2H, d, J=7.2 Hz, CH2CO), 1.99-1.89 (2H, m), 1.86-1.78 (1H, m), 1.71-1.61 (2H, t, J=15 Hz), 1.48-1.45 (3H, d, J=6.9 Hz, Me), 1.33-1.21 (2H, m).

Workup

  1. customto give the corresponding acid, which
  2. customto produce a solid, 0.33 g (50% yield)(procedure D)

Sources & evidence

ORD record
ord-8aca38dc725a4c0a98ad00c6f03dc1b9
Source dataset
uspto-grants-2009_09
Patent number
US07595331B2

Reaction notes

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