N-(2-aminophenyl)-3-(benzyloxy)cyclobutanecarboxamide → 2-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole

HRID 1846813Notes

Reaction equation

HRID 1846813 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH:11]1[CH2:14][CH:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=O>C(O)(=O)C>[CH2:16]([O:15][CH:13]1[CH2:14][CH:11]([C:9]2[NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 67478928N-(2-aminophenyl)-3-(benzyloxy)cyclobutanecarboxamide

Product 1

HCID 674813742-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-aminophenyl)-3-(benzyloxy)cyclobutanecarboxamide (1.78 g, 6.01 mmol) in acetic acid was heated to 100° C. for 1 h, then cooled to RT. The acetic acid was removed in vacuo and ethyl acetate was added to the resulting oil. The resulting suspension was filtered and the collected solid was air dried to give 2-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole. The filtrate was concentrated in vacuo to give another suspension, which was filtered, air dried, and added to the first crop of product to give a total of 0.96 g (3.43 mmol, 57% yield) of 2-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole as a white solid.

Workup

  1. customThe acetic acid was removed in vacuo and ethyl acetate
  2. additionwas added to the resulting oil
  3. filtrationThe resulting suspension was filtered
  4. customdried

Sources & evidence

ORD record
ord-bf13e5d5f2164d6cb61b3aef6506404a
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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