Hydrochloric Acid → HCID 53762829, compound

HRID 1587546Notes

Reaction equation

HRID 1587546 reaction equation
N[CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][NH2:9].[CH3:10][S:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[C:20]([BH3-])#[N:21].[Na+].Cl>CO.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C(O)C>[CH3:10][S:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3][CH2:2][NH:21][CH2:20][C:15]2[CH:18]=[CH:19][C:12]([S:11][CH3:10])=[CH:13][CH:14]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5942Bis(3-aminopropyl)amineHCID 769854-(Methylthio)benzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53762829HCID 53762829, compound

Reagents, catalysts & solvents 3

HCID 6451Bromocresol GreenCatalystHCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

Dissolve 1,5,9-triazanonane (655 mg, 0.005 mol) in methanol (distilled from Mg) (50 mL) and add 4-(methylthio)benzaldehyde (1.52 g, 0.01 mol), sodium cyanoborohydride (0.62 g, 0.010 mol) and 1 drop of 1% bromocresol green in ethanol. Maintain the pH of the reaction with 1N hydrochloric acid in methanol until the indicator no longer changes. Evaporate the solvent in vacuo and partition the residue between 1N sodium hydroxide (50 mL) and ethyl acetate (100 mL). Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo and purify by silica gel chromatography to give the title compound.

Workup

  1. temperatureMaintain
  2. customEvaporate the solvent in vacuo
  3. custompartition the residue between 1N sodium hydroxide (50 mL) and ethyl acetate (100 mL)
  4. customSeparate the organic phase
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-8d4e2f87073d44eeb783819cd9f19bd5
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

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