(R)-Methyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine → HCID 67510514, compound

HRID 1054097Notes

Reaction equation

HRID 1054097 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][N:7]=2)=[CH:2]1.[CH3:14][Mg]Br>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[CH:8][C:9]([CH:10]([OH:11])[CH3:14])=[CH:12][CH:13]=2)=[CH:2]1

Participants

3

Reactant 2

HCID 2764563(R)-Methyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amineHCID 178418573HCID 178418573, compound

Product 1

HCID 67510514HCID 67510514, compound

Procedure

Synthesized using compound 56b (260 mg, 1.37 mmol) and methylmagnesium bromide (2.74 mL, 2.74 mmol, 1 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:1) as eluent. Yellow solid. Yield: 240 mg, 85%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.50 (d, J=6.6 Hz, 3H), 4.90 (q, J=6.3 Hz, 1H), 7.38 (dd, J=5.0, 2.8 Hz, 1H), 7.55 (d, J=8.2 Hz, 1H), 7.61 (dd, J=5.0, 1.3 Hz, 1H), 7.70 (dd, J=8.2, 2.2 Hz, 1H), 7.85 (dd, J=2.8, 1.3 Hz, 1H), 8.48 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=25.2, 68.0, 120.4, 123.6, 126.4, 126.5, 134.3, 139.5, 142.0, 147.4, 152.9; (ESI): m/z=206.29 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-22f3e465dc4f4414abea8a97e774c158
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…