4-Iodoaniline → 1-(4-(4-Aminophenyl)-3-butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

HRID 1279371Notes

Reaction equation

HRID 1279371 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)([OH:11])[CH2:7][CH2:6]1)[CH2:2][C:3]#[CH:4].I[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C(N)CCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:24][C:23]1[CH:25]=[CH:26][C:20]([C:4]#[C:3][CH2:2][CH2:1][N:5]2[CH2:10][CH2:9][C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)([OH:11])[CH2:7][CH2:6]2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 108934-IodoanilineHCID 222257381-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

Product 1

HCID 184280111-(4-(4-Aminophenyl)-3-butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidineYield 21%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8007ButylamineSolvent

Procedure

A solution of 1-(3-butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine (263 mg, 1.00 mmol), 4-iodoaniline (208 mg, 0.950 mmol) and 50 mg of tetrakis(triphenylphosphine) palladium in 10 mL of butylamine is allowed to reflux for 20 hr. The solvent is evaporated in vacuo to give a residue, which is purified by flash chromatography giving the product as an off white solid (70 mg, 21%): mp 134-136° C.; 1H NMR (CDCl3) 1.59 (m, 2 H), 1.90 (m, 2 H), 2.47 (m, 6 H), 2.67 (m, 2 H), 3.59 (S, 1 H), 3.87 (bs, 2 H), 6.46 (d, J=8.1 Hz, 1 H), 7.02 (d, J=8.1 Hz, 2 H), 7.14 (d, J=8.4 Hz, 2 H), 7.33 (d, J=8.4 Hz, 2 H).

Workup

  1. temperatureto reflux for 20 hr
  2. customThe solvent is evaporated in vacuo
  3. customto give a residue, which
  4. customis purified by flash chromatography

Sources & evidence

ORD record
ord-a334544f251b4a4f9cb83c9a941d1b4c
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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