4-Iodoaniline → 1-(4-(4-Aminophenyl)-3-butynyl)-4-(4-chlorobenzyl)piperidine

HRID 1279381Notes

Reaction equation

HRID 1279381 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[CH:16])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.I[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C(N)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:24][C:23]1[CH:25]=[CH:26][C:20]([C:16]#[C:15][CH2:14][CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 108934-IodoanilineHCID 106828724-(4-Chlorobenzyl)-1-(3-butynyl)piperidine

Product 1

HCID 106180251-(4-(4-Aminophenyl)-3-butynyl)-4-(4-chlorobenzyl)piperidineYield 12%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8007ButylamineSolvent

Procedure

To a solution of 4-(4-chlorobenzyl)-1-(but-3-yn-1-yl)piperidine (318 mg, 1.21 mmol) and 4-iodoaniline (265 mg, 2.19 mmol) in 10 mL of butylamine is added 70 mg of Pd(PPh3)4. The resulting solution is allowed to reflux for 24 hr. The solvent is evaporated in vacuo and the residue is purified by flash chromatography giving the title product as a brown oil (50 mg, 12%): 1H NMR (CDCl3) 1.24 (m, 2 H), 1.44 (m, 1 H), 1.58 (m, 2 H), 1.96 ( m, 3 H), 2.15 (m, 2 H), 2.55 (m, 4 H), 2.89 (m, 2 H), 3.75 (bs, 2 H), 6.53 (d, J=6.0 Hz, 2 H), 7.05 (m, 2 H), 7.20 (m, 4 H).

Workup

  1. temperatureto reflux for 24 hr
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-53b0ceb41ec344188db13bb98c1b88a8
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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