Trifluoroacetic acid → (R)-6-chloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole

HRID 1096611Notes

Reaction equation

HRID 1096611 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]3[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]3)[N:7]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])[C:6]=2[CH:28]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]3[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]3)[N:7]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])[C:6]=2[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66786179(R)-tert-butyl 3-(6-chloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 66785643(R)-6-chloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((R)-tert-Butyl 3-(6-chloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (32C) (0.135 mmol, 0.055 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)-6-chloro-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole (32D) as a tan oil that was used directly in the next step without further purification. ESI-MS: m/z 308.3 (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-e200b681f94d406c8ff508e0465a371e
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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