Toluene → HCID 59006379, compound

HRID 2378937Notes

Reaction equation

HRID 2378937 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:15](=O)(O)[O-:16].[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:31][O:32][CH:33]([O:36][CH3:37])[CH2:34][NH2:35]>ClCCl>[CH3:31][O:32][CH:33]([O:36][CH3:37])[CH2:34][NH:35][C:15](=[O:16])[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium BicarbonateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 59006379HCID 59006379, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-1-Boc-piperidine (1.02 g, 5.09 mmol) was dissolved in dichloromethane (25 mL). Aqueous sodium bicarbonate solution was added to the mixture followed by 20% phosgene in toluene (3.2 mL, 6.08 mmol). Mixture stirred vigorously at room temperature for 45 minutes. Aminoacetaldehyde dimethyl acetal (760 μl, 6.98 mmol) was added to the mixture. Reaction stirred vigorously at room temperature for 30 minutes. Reaction layers were partitioned. Aqueous layer was back extracted with dichloromethane and the aqueous phase was discarded. Organic phases were combined. Mixture was dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as pale yellow oil in 96% yield. MS (M−H)−=330.2.

Workup

  1. customReaction
  2. stirringstirred vigorously at room temperature for 30 minutes
  3. customReaction layers
  4. customwere partitioned
  5. extractionAqueous layer was back extracted with dichloromethane
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c0a3ed39d1db41a29bbe1f74a50544c6
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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