Hydrochloric Acid → HCID 49787393, compound

HRID 1951995Notes

Reaction equation

HRID 1951995 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:23][CH3:24])=[C:7]([CH:22]=1)[O:8][CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)#[N:2].Cl>C(O)C>[CH3:24][O:23][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:22][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57476869HCID 57476869, compound

Product 1

HCID 49787393HCID 49787393, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butyl 4-(5-cyano-2-methoxyphenoxy)piperidine-1-carboxylate (2, 39.31 g, 118.26 mmoles) was suspended in ethanol (155.53 g) and heated to 40° C. To this slurry was slowly added HCl (46.61 g, 573.04 mmoles). The mixture was heated to 60° C. and held for 3 hours. The reaction mixture was cooled to 20° C. and seed was charged initiating crystallisation. The resulting solid was isolated by filtration at 0° C., washed twice with ethanol (62.21 g) and then dried to give the title compound as the hydrochloride salt (29.84 g, 77% yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.84 (m, 2H) 2.09 (m, 2H) 3.02 (ddd, J=12.7, 8.9, 3.4 Hz, 2H) 3.20 (m, 2H) 3.84 (s, 3H) 4.63 (tt, J=7.7, 3.6 Hz, 1 H) 7.15 (d, J=8.5 Hz, 1H) 7.45 (dd, J=8.5, 1.9 Hz, 1H) 7.56 (d, J=1.9 Hz, 1H) 9.16 (br. s, 2H); Mass Spectrum: m/z (M+H)+ 233.2.

Workup

  1. temperatureThe mixture was heated to 60° C.
  2. temperatureThe reaction mixture was cooled to 20° C.
  3. additionseed was charged
  4. customcrystallisation
  5. customThe resulting solid was isolated by filtration at 0° C.
  6. washwashed twice with ethanol (62.21 g)
  7. customdried

Sources & evidence

ORD record
ord-bcc72145d54945c4b2958ba8305fea7b
Source dataset
uspto-grants-2013_03
Patent number
US08404839B2

Reaction notes

Loading…