Triethylamine → HCID 86670987, compound

HRID 515359Notes

Reaction equation

HRID 515359 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O-:4])=[O:3].C(N(CC)CC)C.Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([OH:42])([C:38]([F:41])([F:40])[F:39])[C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=1>ClCCl>[F:35][C:34]([F:36])([F:37])[C:33]([C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:15]=[CH:16][CH:17]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=3)[CH2:14][CH2:13]2)=[CH:28][CH:29]=1)([OH:42])[C:38]([F:39])([F:41])[F:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 224033414-(3-Nitrophenoxy)piperidine--hydrogen chloride (1/1)HCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86670987HCID 86670987, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-(3-nitrophenoxy)piperidine hydrochloride (11.87 mmol, 3.07 g) and triethylamine (35.6 mmol, 4.96 mL, 3.60 g) in dichloromethane was added 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (11.87 mmol, 4.00 g). The reaction was stirred for 20 hours then was filtered. The filtrate was chromatographed on silica (eluting with a gradient of dichloromethane to ethyl acetate) to give the title compound (4 g). MS (ESI) m/z 479.0 [M+H]+

Workup

  1. filtrationthen was filtered
  2. customThe filtrate was chromatographed on silica (
  3. washeluting with a gradient of dichloromethane to ethyl acetate)

Sources & evidence

ORD record
ord-75677b129280453ba4c5370261ba373a
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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