Ammonium Chloride → Benzyl 3-(2-amino-1-(5-morpholino-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate

HRID 2361344Notes

Reaction equation

HRID 2361344 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][N+:10]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>CO.O1CCCC1.[Zn]>[NH2:10][CH2:9][CH:8]([C:7]1[C:2]([CH3:1])=[C:3]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:4]=[CH:5][CH:6]=1)[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[CH:20]=2)[NH:15][CH:14]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67994839Benzyl 2-methyl-3-(1-(5-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate

Product 1

HCID 67995166Benzyl 3-(2-amino-1-(5-morpholino-1H-indol-3-yl)ethyl)-2-methylphenylcarbamateYield 86%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 2-methyl-3-(1-(5-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate (0.8011 g, 1.557 mmol), ammonium chloride (1.249 g, 23.35 mmol) and zinc (1.527 g, 23.35 mmol) in methanol (32.4 mL) and tetrahydrofuran (32.4 mL) was stirred for 2 hr. The reaction was filtered through a pad of CELITE® and rinsed with methanol. The filtrate was concentrated in vacuo, dissolved in EtOAc and water. The layers were separated, and the aqueous layer was extracted with EtOAc (6×). The aqueous layer was basified by NaHCO3 (s) and extracted with EtOAc (3×). The organic layers were combined, dried over MgSO4, and concentrated in vacuo to give the desired product (0.7121 g, 1.337 mmol, 86% yield) as a tan solid.

Workup

  1. filtrationThe reaction was filtered through a pad of CELITE®
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutiondissolved in EtOAc
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (6×)
  7. extractionextracted with EtOAc (3×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2513c105a014ce19fda444c9555720b
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…