Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][N:21]3[C:24](=[O:26])[CH3:25])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCCC(=O)C1)C1C=CC=CC=1.C(N1C2C(=CC=C(N)C=2)CC1)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.[C:72](Cl)(=[O:81])[CH:73]=[CH:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1>ClCCCl>[C:24]([N:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([N:14]([CH:10]3[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9]3)[C:72](=[O:81])/[CH:73]=[CH:74]/[C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)[CH:23]=2)[CH2:19][CH2:20]1)(=[O:26])[CH3:25]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
1-[6-(1-Benzyl-piperidin-3-ylamino)-2,3-dihydro-indol-1-yl]-ethanone. The desired intermediate (116 mg, 30%) was prepared as in Example 39, Step A, employing 1-benzyl-3-piperidone (510 mg, 4.4 mmol), 1-acetyl-6-aminoindoline (200 mg, 1 mmol), Na(OAc)3BH (910 mg, 4.3 mmol), and AcOH (340 μL, 5.4 mmol) in 1,2-dichloroethane (20 mL). Step B. The above intermediate (0.10 g, 0.29 mmol) was then reacted with cinnamoyl chloride (62 mg, 0.37 mmol) as in Example 2, Step C to provide 145 mg (99%) of the desired product. 1H NMR (500 MHz, CDCl3): 8.04 (s, 1H), 7.62 (d, J=15.5 Hz, 1H), 7.30-7.18 (m, 10H), 7.15 (d, J=7.8 Hz, 1H), 6.74 (dd, J=7.3, 1.4 Hz, 1H), 6.16 (d, J=15.5 Hz, 1H), 4.79-4.68 (m, 1H), 4.18-4.07 (m, 2H), 3.30-3.15 (m, 2H), 2.98-2.85 (m, 2H), 2.26-2.23 (m, 2H), 2.21 (s, 3H), 2.15-2.01 (m, 2H), 1.93-1.75 (m, 2H), 1.60-1.35 (m, 3H). MS: exact mass calculated for C31H33N3O2, 479.26; m/z found, 480.2 [M+H]+.
Sources & evidence
- ORD record
- ord-e07c973fcfde486ca4597e35b471eca4
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317025B2
Linked notes
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