Hydrochloric Acid → HCID 21882797, compound

HRID 722133Notes

Reaction equation

HRID 722133 reaction equation
C([BH3-])#N.[Na+].[N+:5]([C:8]1[CH:19]=[CH:18][C:17]2[CH2:16][CH:15]3[C:20](=[N:21][OH:22])[CH:12]([CH2:13][CH2:14]3)[CH2:11][C:10]=2[CH:9]=1)([O-:7])=[O:6].Cl.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C>CO.[OH-].[Na+]>[N+:5]([C:8]1[CH:19]=[CH:18][C:17]2[CH2:16][CH:15]3[CH:20]([NH:21][OH:22])[CH:12]([CH2:13][CH2:14]3)[CH2:11][C:10]=2[CH:9]=1)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 58926596HCID 58926596, compound

Product 1

HCID 21882797HCID 21882797, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium cyanoborohydride (255 mg) was added in a single portion to a solution of the oxime of Step 1 (500 mg) in dry methanol (20 mL) at −20° C. 2N HCl was then added until the solution was at pH 3 (Methyl Orange). After 3 hours the reaction was diluted with 4N NaOH (50 mL) and reduced to 1/3 volume. The residue was extracted with DCM (4×50 mL), the organic layers combined and dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound as a white foam (477 mg). m/z 249 (M+H+). Step 3: Tricyclo[8.2.1.03,8]trideca-3(8),4,6-triene-5,13-diamine

Workup

  1. extractionThe residue was extracted with DCM (4×50 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7bdace38c21e4011a0300fd5ae96c7aa
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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