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

HRID 1279366Notes

Reaction equation

HRID 1279366 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:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>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>[NH2:23][C:22]1[CH:21]=[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:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 122713-IodoanilineHCID 222257381-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

Product 1

HCID 184280081-(4-(3-Aminophenyl)-3-butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidineYield 69%

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), 3-iodoaniline (208 mg, 0.950 mmol) and tetrakis(triphenylphosphine) palladium (0) (46 mg) in n-butylamine (5 mL) is allowed to reflux for 15 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 (231 mg, 69%): mp 139-140° C.; 1H NMR (CDCl3) 1.71 (m, 3 H), 2.12 (m, 2 H), 2.56 (m, 4 H), 2.73 (m, 2 H), 2.84 (m, 2 H), 3.60 (bs, 2 H), 6.59 (d, J=7.5 Hz, 1 H), 6.72 (s, 1 H), 6.79 (d, J=7.5 Hz, 1 H), 7.07 (dd, J1=J2=7.5 Hz, 1 H), 7.33 (d, J=9.7 Hz, 2 H), 7.46 (d, J=9.7 Hz, 2 H).

Workup

  1. temperatureto reflux for 15 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-68f925ccc2df4f5e8399fa4d856af907
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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