Tert-Butyl nitrite → HCID 136342879, compound

HRID 1175118Notes

Reaction equation

HRID 1175118 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.CC([O-])(C)C.[K+].[N:18](OC(C)(C)C)=[O:19]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[N:18][OH:19])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 23665647Potassium tert-butoxideHCID 56737780HCID 56737780, compound

Product 1

HCID 136342879HCID 136342879, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Chloro-5,6,7,8-tetrahydro-isoquinoline (Chemische Berichte 1948, 81, 279) (8.82 g; 52.6 mmol) dissolved in THF (65 ml) is added under stirring at room temperature to a solution of KOtBu (11.78 g; 105.2 mmol) in THF (100 ml). The red turbid solution is stirred for 12 hours and then cooled to 0° C. tert-Butyl nitrite (18.7 ml; 157.8 mmol) is added dropwise, the reaction mixture is stirred at room temperature for 4 hours and poured on brine. The reaction mixture is extracted with ethyl acetate three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as brownish crystals. 1H-NMR (400 MHz; DMSO-d6): 11.83 (s, 1H); 8.28 (s, 1H); 7.66 (s, 1H); 2.72 (m, 2H); 2.66 (m, 2H); 1.77 (m, 2H). MS (m/z) ES+: (197, MH+).

Workup

  1. additionis added
  2. additionis added dropwise
  3. stirringthe reaction mixture is stirred at room temperature for 4 hours
  4. additionpoured on brine
  5. extractionThe reaction mixture is extracted with ethyl acetate three times
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d0309cd7988c433582f82cac8c631b8b
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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