Sodium Bicarbonate → HCID 21109932, compound

HRID 1766183Notes

Reaction equation

HRID 1766183 reaction equation
[O-:1][C:2]#[N:3].[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][N:13]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[NH2:3][C:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][N:13]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19]1)=[O:1]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 21109928HCID 21109928, compound

Product 1

HCID 21109932HCID 21109932, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2.0 g (0.03 mol) of sodium cyanate were added to a solution of 7.91 g (0.02 mol) of N-[(2-aminophenyl)methyl]-N-(1,1-dimethylethoxycarbonyl)-1-(phenylmethyl)-4-piperidineamine in a mixture of 5.5 ml glacial acetic acid and 80 ml of water and the mixture was stirred overnight at ambient temperature. The mixture was made slightly alkaline by the addition of saturated sodium hydrogen carbonate solution, then extracted exhaustively with EE. The combined ethyl acetate extracts were washed with water, dried over sodium sulphate and concentrated by evaporation in vacuo. 8.7 g (99% of theoretical) of colourless crystals were obtained, Rf 0.71 (El D), which were further processed without any additional purification.

Workup

  1. extractionextracted exhaustively with EE
  2. washThe combined ethyl acetate extracts were washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. custom8.7 g (99% of theoretical) of colourless crystals were obtained
  6. customRf 0.71 (El D), which were further processed without any additional purification

Sources & evidence

ORD record
ord-b334dfb25c2e49838a3c73a040c25047
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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