Sodium Carbonate → HCID 22266170, compound

HRID 489601Notes

Reaction equation

HRID 489601 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2([C:22]#[N:23])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[C:24](=[O:27])([O-])[O-:25].[Na+].[Na+]>ClCCl.C(N(CC)CC)C.ClC(OCC1C=CC=CC=1)=O>[CH2:2]([O:25][C:24]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2([C:22]#[N:23])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1)=[O:27])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 22265958HCID 22265958, compound

Product 1

HCID 22266170HCID 22266170, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 10387Benzyl chloroformateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.2 g of 4-(3-Aminomethyl-phenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrile in 15 ml of dichloromethane was added a few drops of triethylamine followed by a few drops of benzyl chloroformate. The mixture was stirred for 1 hour at room temperature and was poured into aqueous sodium carbonate and was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and was filtered. The filtrate was evaporated and the residue was used directly in the next step without further purification: 1H-NMR (300 MHz, CDCl3)δ (TMS) 1.39-1.52 (m, 9H), 1.80-2.16(m, 4H), 3.08-3.42(m, 4H), 4.19-4.50(m, 2H), 5.08-5.13(d, 2H), 7.28-7.79(m, 9H), MS (ESI) m/e 450 (M+H)+.

Workup

  1. extractionwas extracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationwas filtered
  4. customThe filtrate was evaporated
  5. customthe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-44520455fadf4012978189d6a47e4642
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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