Hexylamine → HCID 10609701, compound

HRID 412778Notes

Reaction equation

HRID 412778 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([NH2:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].CC(C)([O-])C.[Na+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:12]([NH:18][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 8102HexylamineHCID 775951-Bromo-4-tert-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 10609701HCID 10609701, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

According to the general procedure B, 4-tert-butylbromobenzene (108 mg, 0.51 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (59 mg, 0.60 mmol) in THF at 80° C. for 2 h to give the title compound (110 mg, 94%) as a colorless oil: 1H-NMR (300 MHz, CDCl3): δ 7.26 (d, 2H, J=8.4 Hz), 6.62 (d, 2H, J=8.4 Hz), 3.51 (bs, 1H), 3.14 (t, 2H, J=7.2 Hz), 1.66 (m, 2H), 1.34-1.43 (m, 6H), 1.34 (s, 9H, t-Bu), 0.96 (t, 3H, J=6.3 and 6.9 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.14, 139.75, 125.92, 112.35, 44.11, 33.76, 31.63, 31.53, 29.58, 26.86, 22.62, 14.05. GC/MS(EI): m/z 233 (M+). Anal. Calcd for C16H27N: C, 82.34; H, 11.82; N, 6.00. Found: C,82.55; H, 11.82; N, 6.06.

Workup

  1. customat 80° C.
  2. customfor 2 h

Sources & evidence

ORD record
ord-ddf93d5b4f5842748d109c27835a96fa
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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