Sodium Hydroxide → 1,1-Dimethylethyl N-[2-oxo-2-[[1-(phenylmethyl)-4-piperidinyl]amino]ethyl]carbamate

HRID 133580Notes

Reaction equation

HRID 133580 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:34][CH:35]1[CH2:40][CH2:39][N:38]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:37][CH2:36]1.[OH-].[Na+]>ClCCl>[CH2:41]([N:38]1[CH2:39][CH2:40][CH:35]([NH:34][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:37]1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 184261311,1-Dimethylethyl N-[2-oxo-2-[[1-(phenylmethyl)-4-piperidinyl]amino]ethyl]carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)glycine (3.48 g, 20 mmol), EDCI (4.02 g, 21 mmol) and HOBt (2.83 g, 21 mmol) were added to a dichloromethane (40 mL) solution of 4- amino-1-benzylpiperidine (3.80 g, 20 mmol). The resulting reaction mixture was stirred at room temperature for 12 hours, and a 2 M solution of NaOH was then added. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL×2). The organic layers were combined, washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate/methanol/triethylamine=85:12:3) to afford 1-benzyl-4-[[N-(tert-butoxycarbonyl)glycyl]amino]piperidine (6.59 g, 95%).

Workup

  1. customThe resulting reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (20 mL×2)
  4. washwashed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained crude product
  9. customwas purified by column chromatography (SiO2, ethyl acetate/methanol/triethylamine=85:12:3)

Sources & evidence

ORD record
ord-b575b579a2e94dadb1168ae03c2bb9e4
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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