N-(3-{1-[5-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-YL)pentyl]4-piperidinyl}phenyl)-2-methylpropanamide → N-(3-{1-[4-(1,3-Dioxo-1,3-Dihydro-2H-Isoindol-2-yl)Butyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

HRID 1832166Notes

Reaction equation

HRID 1832166 reaction equation
C1(C2CCN(CC[CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])CC2)C=CC=CC=1.O=C1C2C(=CC=CC=2)C(=O)N1CCCCC[N:46]1[CH2:51][CH2:50][CH:49]([C:52]2[CH:53]=[C:54]([NH:58][C:59](=[O:63])[CH:60]([CH3:62])[CH3:61])[CH:55]=[CH:56][CH:57]=2)[CH2:48][CH2:47]1>>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[CH2:18][CH2:17][CH2:16][CH2:15][N:46]1[CH2:51][CH2:50][CH:49]([C:52]2[CH:53]=[C:54]([NH:58][C:59](=[O:63])[CH:60]([CH3:62])[CH3:61])[CH:55]=[CH:56][CH:57]=2)[CH2:48][CH2:47]1

Participants

3

Reactant 2

HCID 16757160N-(3-{1-[5-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-YL)pentyl]4-piperidinyl}phenyl)-2-methylpropanamideHCID 220486382-[6-(4-Phenyl-1-Piperidinyl)Hexyl]-1H-Isoindole-1,3(2H)-Dione

Product 1

HCID 16757363N-(3-{1-[4-(1,3-Dioxo-1,3-Dihydro-2H-Isoindol-2-yl)Butyl]-4-Piperidinyl}Phenyl)-2-MethylpropanamideYield 64%

Procedure

The synthetic method is the same as described for 2-[6-(4-phenyl-1-piperidinyl)hexyl]-1H-isoindole-1,3(2H)-dione. N-(3-{1-[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentyl]-4-piperidinyl}phenyl)-2-methylpropanamide: 614 mg (64% yield); 1H NMR (400 MHz, CDCl3) δ 7.87–7.8 (m, 2H), 7.76–7.68 (m, 2H), 7.48 (s, 1H), 7.41 (d, 1H, J=7.6 Hz), 7.21 (t, 1H, J=7.6 Hz), 6.95 (d, 1H, J=7.6 Hz), 3.69 (t, 2H, J=7.2 Hz), 3.39–3.28 (m, 2H), 3.02 (apparent d, 2H, J=11.6 Hz), 2.78 (q, 2H, J=7.2 Hz), 2.64–2.52 (m, 1H), 2.52–2.40 (m, 1H), 2.40–2.31 (m, 2H), 2.01 (dt, 2H, J=3.7, 11.1 Hz), 1.85–1.64 (m, 2H), 1.58 (q, 2H, J=7.6 Hz), 1.45–1.32 (m, 2H), 1.23 (d, 6H, J=6.9 Hz); ESMS m/e: 462.4 (M+H)+; Anal. Calc. for C28H36N3ClO3: C, 67.52; H, 7.29; N, 8.44. Found: C, 67.04; H, 7.06; N, 8.38.

Sources & evidence

ORD record
ord-087caea8949c4027a99ea5d11f3f09f2
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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