Diisopropylethylamine → HCID 68853923, compound

HRID 1500271Notes

Reaction equation

HRID 1500271 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20](F)[CH:19]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:22]2[CH:23]=[C:18]([Br:17])[CH:19]=[CH:20][C:21]=2[N+:24]([O-:26])=[O:25])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 4362805tert-Butyl [2-(piperidin-3-yl)ethyl]carbamate

Product 1

HCID 68853923HCID 68853923, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2-Piperidin-3-yl-ethyl)-carbamic acid tert-butyl ester (0.087 mmol, 0.020 g) and 4-Bromo-2-fluoronitrobenzene (1.0 eq, 0.019 g), N,N-diisopropylethylamine (1.2 eq, 13.5 μL) in ACN (2 mL) was irradiated using microwave for 18 minutes at a temperature of 130° C. The solution was then cooled to room temperature and concentrated in vacuo to provide {2-[1-(5-Bromo-2-nitro-phenyl)-piperidin-3-yl]-ethyl}-carbamic acid tert-butyl ester. HPLC-MS RT=2.37 min, mass calculated for formula C18H26BrN3O4 427.11, observed LCMS m/z 428.22 and 430.11 (M+H).

Workup

  1. customfor 18 minutes
  2. customat a temperature of 130° C
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a19db74f95cf4f7ab38f242b223781a2
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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