4-(2-Aminoethyl)piperidine, 4-BOC protected → HCID 66819012, compound

HRID 1024742Notes

Reaction equation

[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([O:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[C:11](O)=[O:12])=[CH:5][CH:4]=1)#[N:2].[C:28]([O:32][C:33](=[O:43])[NH:34][CH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33](=[O:43])[NH:34][CH2:35][CH2:36][CH:37]1[CH2:38][CH2:39][N:40]([C:11](=[O:12])[C:10]2[CH:14]=[C:15]([O:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[C:8]([O:7][C:6]3[CH:26]=[CH:27][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH:9]=2)[CH2:41][CH2:42]1)([CH3:31])([CH3:29])[CH3:30]

Participants

Reactant 2

HCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protected

HCID 66818728HCID 66818728, compound

Product 1

HCID 66819012HCID 66819012, compoundYield 58.2%

Procedure

Following the procedure of Example 5(c) 3-(4-cyano phenoxy)-5-phenethyloxy benzoic acid 0.6 g (1.66 mmol) and (2-piperidin-4-yl-ethyl)-carbamic acid tert-butyl ester (0.378 g, 1.66 mmol) were used to afford 0.55 g of the required product. 1H NMR (DMSO-d6): δ 1.05 (3H, m), 1.4 (9H, s), 1.55 (2H, m), 1.7 (1H, m), 2.1 (5H, s), 3.0 (5H, m), 4.2 (2H, t), 4.4 (1H, m), 6.62 (1H, s), 6.78 (2H, s), 7.14 (2H, d), 7.24 (1H, m), 7.3 (4H, d), 7.88 (2H, d).

Sources & evidence

ORD record: ord-0acfa16cbbf94484aa993d63621417a9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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