Sodium Azide → HCID 89964488, compound

HRID 1846211Notes

Reaction equation

HRID 1846211 reaction equation
[N:1]([C:4]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].FC(F)(F)C1C=CC(C2(O)C3N=CC=CC=3CCC2)=CC=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.[N-]=[N+]=[N-].[Na+]>CCOC(C)=O.O.C1(C)C=CC=CC=1>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([C:4]2([NH2:1])[C:13]3[N:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:7][CH2:6][CH2:5]2)=[CH:15][CH:16]=1

Participants

9

Reactant 5

HCID 33557Sodium AzideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 89964608HCID 89964608, compoundHCID 89964803HCID 89964803, compound

Product 1

HCID 89964488HCID 89964488, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-azido-8-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroquinoline. To a solution of 8-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroquinolin-8-ol (1.2 g, 4.09 mmol) and toluene (2.5 mL) was added DPPA (2.7 mL, 12.53 mmol) and DBU (0.77 mL, 5.11 mmol). The reaction was then treated with sodium azide (780 mg, 12.00 mmol) and stirred for 2 days. The reaction was poured into a separatory funnel containing water and EtOAc. The aqueous layer was extracted with EtOAc (2×25 mL). The combined EtOAc layers were concentrated in vacuo and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with 0-40% EtOAc in hexane, to provide the title compound as a colorless oil. MS (ESI pos. ion) m/z: 319.0 (MH+).

Workup

  1. additionThe reaction was poured into a separatory funnel
  2. extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
  3. concentrationThe combined EtOAc layers were concentrated in vacuo
  4. customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
  5. washeluting with 0-40% EtOAc in hexane

Sources & evidence

ORD record
ord-2383e525683846feb01df514b6c7ea9f
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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