4-(2-Aminoethyl)piperidine, 4-BOC protected → HCID 66818684, compound

HRID 1024744Notes

Reaction equation

HRID 1024744 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[CH:17]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1)#[N:2].[C:29]([O:33][C:34](=[O:44])[NH:35][CH2:36][CH2:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34](=[O:44])[NH:35][CH2:36][CH2:37][CH:38]1[CH2:39][CH2:40][N:41]([C:12](=[O:14])[C:11]2[CH:15]=[C:16]([O:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=3)[CH:17]=[C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:28][CH:27]=3)[CH:10]=2)[CH2:42][CH2:43]1)([CH3:32])([CH3:30])[CH3:31]

Participants

3

Reactant 2

HCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 66818681HCID 66818681, compound

Product 1

HCID 66818684HCID 66818684, compoundYield 73.4%

Procedure

Following the procedure of Example 5(c) 3-(4-cyano-benzyloxy)-5-(4-cyano-phenoxy)-benzoic acid 0.8 g (2.16 mmol) and (2-piperidin-4-yl-ethyl)-carbamic acid tert-butyl ester (0.49 g, 2.16 mmol) were used to afford 0.92 g of the required product. 1H NMR (DMSO-d6): δ 1.10 (2H, m), 1.30 (2H, m), 1.4 (9H, s), 1.50 (2H, m), 1.75 (1H, m), 2.70 (1H, m), 2.8 (3H, m), 3.5 (1H, m), 4.4 (1H, m), 5.2 (2H, s), 6.65 (1H, s), 6.78 (1H, m), 6.88 (2H, m), 7.16 (2H, s), 7.64 (2H, d), 7.88 (4H, m).

Sources & evidence

ORD record
ord-9d7e7c7eb29a4175a3995ca773b17c21
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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