Piperidine → N-(4-Amino-2-benzyloxy-phenyl)-2-benzyloxy-nicotinamide

HRID 1354867Notes

Reaction equation

HRID 1354867 reaction equation
C1C2C(COC(=O)[NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[C:28]([O:33][CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:26])=[C:20]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:19]=3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C1COCC1.CN(C=O)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:26])[C:27]2[CH:32]=[CH:31][CH:30]=[N:29][C:28]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:20]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:19]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 58865748HCID 58865748, compound

Product 1

HCID 21104163N-(4-Amino-2-benzyloxy-phenyl)-2-benzyloxy-nicotinamideYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

{3-Benzyloxy-4-[(2-benzyloxy-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (424) (0.430 g, 0.664 mmol) was dissolved in a mixture of THF (6 mL) and DMF (3 mL). Piperidine (12.88 mmol) was added. The mixture was shaken at room temperature for 1 h. LC-MS indicated complete de-protection at this point. The mixture was concentrated under reduced pressure to give a dark brown/purple oil. Purification by flash chromatography on silica gel using a gradient of hexane and EtOAc (15–100% EtOAc/hexane 25 minutes) gave the desired product (425) as an orange oil upon concentration (0.229 g, 0.538 mmol, 81% yield). LC-MS (ESI): (exact mass: 425.17) m/e=426.2 [M+1]+ (100%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a dark brown/purple oil
  3. customPurification by flash chromatography on silica gel using a gradient of hexane and EtOAc (15–100% EtOAc/hexane 25 minutes)

Sources & evidence

ORD record
ord-cadfe77b409f4ccc8a5858508b539f84
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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