Hexylamine → Methyl 4-(hexylamino)benzoate

HRID 412790Notes

Reaction equation

HRID 412790 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([NH2:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([NH:18][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 8102HexylamineHCID 14307Methyl 4-chlorobenzoateHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 12045719Methyl 4-(hexylamino)benzoateYield 86%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, Methyl 4-chlorobenzoate (85 mg, 0.50 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 2 mol % of Pd(dba)2, 4 mol % of Ph5FcP(t-Bu)2, K3PO4 (260 mg, 1.23 mmol) in toluene at 100° C. for 20 h to give the title compound (101 mg, 86%) as a solid: 1H-NMR (500 MHz, CDCl3): δ 7.90 (d, 2H, J=8.8 Hz), 6.54 (d, 2H, J=8.8 Hz), 4.17 (bs, 1H), 3.85 (s, 3H, —COOMe), 3.15 (dd, 2H, J=7.0 and 12.3 Hz), 1.62 (m, 2H), 1.40 (m, 2H), 1.32 (m, 2H), 0.91 (t, 3H, J=6.9 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 167.31, 152.13, 131.47, 117.85, 111.22, 51.38, 43.30, 31.50, 29.21, 26.68, 22.52, 13.94. GC/MS(EI): m/z 235 (M+), 164. Anal. Calcd for C14H21NO2: C, 71.46; H, 8.99; N, 5.95. Found: C, 71.54; H, 8.84; N, 5.79.

Workup

  1. customat 100° C.
  2. customfor 20 h

Sources & evidence

ORD record
ord-6223643c978b4dac8de8b70e14d1d7ae
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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