Trifluoroacetic acid → (R)-7-Chloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole

HRID 1096605Notes

Reaction equation

HRID 1096605 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[C:9]([C@@H:11]3[CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]3)=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]2[N:8]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[C:9]([C@@H:11]3[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66785572(R)-tert-butyl 3-(7-chloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 66786365(R)-7-Chloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 3-(7-chloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (0.222 mmol, 0.090 g) was added to a 10 mL round-bottomed flask equipped for stirring under nitrogen. Dichloromethane (1 mL) and trifluoroacetic acid (1 mL) were then added and the resultant solution was allowed to stir under nitrogen for 4 hr. The reaction was then concentrated and dried in-vacuo affording (R)-7-Chloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole (30E) a brown oil and used without further purification. ESI-MS: m/z 308.2 (M+H)+.

Workup

  1. customequipped
  2. stirringto stir under nitrogen for 4 hr
  3. concentrationThe reaction was then concentrated
  4. customdried in-vacuo

Sources & evidence

ORD record
ord-45e311adbf4c4c9589241ff9de6370c5
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

Loading…