Triethylamine → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-pyridylmethylamino)-2-butynyl]-2-(2-naphthylmethyl)piperazine trihydrochloride

HRID 584191Notes

Reaction equation

HRID 584191 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][Cl:18])[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:7].[NH2:39][CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1.C(N(CC)CC)C>C(#N)C>[ClH:18].[ClH:18].[ClH:18].[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][NH:39][CH2:40][C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)[CH2:10][C@H:9]1[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 53862488(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(4-chloro-2-butynyl)-2-(2-naphthylmethyl)piperazine

Product 1

HCID 86596428(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-pyridylmethylamino)-2-butynyl]-2-(2-naphthylmethyl)piperazine trihydrochlorideYield 67.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(4-chloro-2-butynyl)-2-(2-naphthylmethyl)piperazine (200 mg), 3-(aminomethyl)pyridine (47 mg), and triethylamine (0.08 ml) in acetonitrile (2 ml) was stirred under reflux for 3 hours and evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (10 ml) using dichloromethane-methanol (30:1) as eluent. The obtained oil was dissolved in ethyl acetate and treated with a solution of,4N hydrogen chloride in ethyl acetate. The mixture was evaporated under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3-pyridylmethylamino)-2-butynyl]-2-(2-naphthylmethyl)piperazine trihydrochloride (60 mg) as a powder.

Workup

  1. temperatureunder reflux for 3 hours
  2. customevaporated under reduced pressure
  3. customThe obtained residue was purified by column chromatography on silica gel (10 ml)
  4. dissolutionThe obtained oil was dissolved in ethyl acetate
  5. additiontreated with a solution of,4N hydrogen chloride in ethyl acetate
  6. customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9dd6b92cc1cd44c3bbbba11f3b883b51
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

Loading…