Triethylamine → HCID 86638580, compound

HRID 1807796Notes

Reaction equation

HRID 1807796 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.Br[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[CH:34]=1>ClCCl.C(=O)([O-])O.[Na+]>[F:23][C:2]([F:22])([F:1])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[CH:34]=3)[CH2:20][CH2:21]2)=[CH:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

Product 1

HCID 86638580HCID 86638580, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)-propan-2-ol (3.21 mmol, 1.1 g) and triethylamine (3.21 mmol, 0.448 ml, 0.325 g) in dichloromethane was added 1-(bromomethyl)-3-nitrobenzene (3.21 mmol, 0.694 g). The reaction was stirred for 20 hours then was diluted with dichloromethane and sodium hydrogen carbonate (aqueous). The organic layer was separated and poured onto a SCX column. The column was eluted with 2M ammonia in methanol and concentrated under reduced pressure to give the title compound (1 g). MS (ESI) m/z 478.1 [M+H]+

Workup

  1. customThe organic layer was separated
  2. additionpoured onto a SCX column
  3. washThe column was eluted with 2M ammonia in methanol
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-764e65859f3f4e1cbf816a25fab1a4bc
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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