Water → HCID 58994384, compound

HRID 1190226Notes

Reaction equation

HRID 1190226 reaction equation
[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].O.[NH4+].[Cl-]>CO.[Zn]>[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[CH2:13][CH2:14]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58994589HCID 58994589, compound

Product 1

HCID 58994384HCID 58994384, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(4-nitro-benzyl)-piperazine (as prepared in the previous step, 279 mg, 0.735 mmol) in MeOH (4 mL) and water (4 mL) was treated with solid NH4Cl (393 mg, 7.35 mmol) and Zn powder (240 mg, 3.67 mmol). The mixture was stirred at 50° C. for 2 h and at RT for 16 h. The mixture was partitioned between EtOAc and water. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification of the residue on a 20-g Isolute SPE column on a FlashMaster system with EtOAc afforded the title compound (204 mg, 79%) as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C19H35N3OSi, 350.3 (M+H). found 350.2.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue on a 20-g Isolute SPE column on a FlashMaster system with EtOAc

Sources & evidence

ORD record
ord-11a52566196e4e84948650e96a12eb96
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…