4-Bromobenzophenone → [4-(Hexylamino)phenyl](phenyl)methanone

HRID 412777Notes

Reaction equation

HRID 412777 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]([NH2:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].CC(C)([O-])C.[Na+]>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]>[CH2:16]([NH:22][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 70304-BromobenzophenoneHCID 8102HexylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 69387344[4-(Hexylamino)phenyl](phenyl)methanoneYield 95.2%

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, 4-Bromobenzophenone (131 mg, 0.50 mmol) reacted with n-hexylamine (52 mg, 0.52 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 50° C. for 13 h to give the title compound (134 mg, 93%) as a solid: 1H-NMR (300 MHz, CDCl3): δ 7.74, (t, 4H, J=8.4 Hz), 7.53-7.43 (m, 3H), 6.58 (d, 2H, J=8.7 Hz), 4.46 (bs, 1H), 3.17 (t, 2H, J=6.6 Hz), 1.61 (m, 2H), 1.42-1.32 (m, 6H), 0.91 (t, 3H, J=6.6 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 195.00, 152.27, 139.11, 132.93, 131.00, 129.30, 127.89, 125.42, 111.02, 43.17, 31.44, 29.09. GC/MS(EI): m/z 281 (M+).

Workup

  1. customat 50° C.
  2. customfor 13 h

Sources & evidence

ORD record
ord-6dd6441efdca4edf83ccde4f8576471e
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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