Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate → 3-[1-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoic acid

HRID 1291850Notes

Reaction equation

HRID 1291850 reaction equation
C(OC(N1CCC(CCC(OCC)=O)CC1)=O)C1C=CC=CC=1.[N:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][N:33]([CH2:36][C:37]([N:39]3[CH2:44][CH2:43][CH:42]([CH2:45][CH2:46][C:47]([O:49]CC)=[O:48])[CH2:41][CH2:40]3)=[O:38])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1>>[N:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:31][CH2:32][N:33]([CH2:36][C:37]([N:39]3[CH2:40][CH2:41][CH:42]([CH2:45][CH2:46][C:47]([OH:49])=[O:48])[CH2:43][CH2:44]3)=[O:38])[CH2:34][CH2:35]2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 14989191Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylateHCID 18918542Ethyl 3-[1-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoate2×

Product 1

HCID 189186023-[1-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoic acid

Procedure

In a similar manner to that described in Example 103, ethyl 3-(1-benzyloxycarbonylpiperidin-4-yl)propanoate was converted to ethyl 3-[1-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoate. The following intermediates were isolated: ethyl-1-bromoacetylpiperidin-4-ylpropanoate. NMR(CDCl3): δ, 1.1-1.4(2H,m); 1.25(3H,t); 1.5-1.7(3H,m); 1.7-1.9(2H,t); 2.3(2H,t); 2.5-2.7(1H,td); 3.0-3.2(1H,td); 3.8-4.0(2H,d+1H,m); 4.15(2H,q); 4.55(1H,m); m/e 306/308(M+H)+, ethyl 3-[1-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]piperidin-4-yl]propanoate. m.p. 90°-92° C.; NMR(d6DMSO): δ, 0.85-1.0(1H,m); 1.05-1.2(1H,m); 1.2(3H,t); 1.5(3H,m); 1.7(2H,m); 2.3(2H,t); 2.5(4H,br.s); 2.8-3.0(1H,t); 3.1(1H,d); 4.05(2H,q+1H,m); 4.3(1H,d); 6.8(2H,d); 8.15(2H,d); m/e 389 (M+H)+ 411 (M+Na)+ ; calculated for C21H32N4O3 ; C, 64.9; H, 8.3; N, 14.4; found: C, 65.0; H, 8.5; N, 14.4%.

Workup

  1. customThe following intermediates were isolated

Sources & evidence

ORD record
ord-b88e7b9745974aa8873cb8ae9c43716f
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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