Water → HCID 178419544, compound

HRID 415057Notes

Reaction equation

HRID 415057 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[NH2:23])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.O.[N:25]#[C:26][Br:27]>C(#N)C>[BrH:27].[NH2:25][C:26]1[NH:23][C:22]2[CH:21]=[CH:20][C:4]([O:5][CH2:6][CH:7]3[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:9][CH2:8]3)=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 59349554HCID 59349554, compound

Product 1

HCID 178419544HCID 178419544, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 4-((3,4-diaminophenoxy)methyl)piperidine-1-carboxylate (10.18 mmoles, 3.27 g, 1 equivalent) was dissolved in acetonitrile (40 ml) and water (20 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (1.112 g, 10.5 mmoles) was added in one lot and the reaction mixture was allowed to go to room temperature and stirred for 16 hours. The reaction mixture was then evaporated under reduced pressure to give 3.53 g of tert-butyl 4-((2-amino-1H-benzo[d]imidazol-5-yloxy)methyl)piperidine-1-carboxylate hydrobromide (yield n 100%) which was used directly in the next step without any further purification. 1H-NMR (400 MHz, DMSO-d6) δ 12.22 (br s, 2H), 8.30 (s, 2H), 7.21 (d, 1H), 6.90 (s, 1H), 6.79 (d, 1H), 3.96 (m, 2H), 3.82 (d, 2H), 2.73 (m, 2H), 1.91 (m, 1H), 1.74 (d, 2H), 1.39 (s, 9H), 1.26 (m, 2H). MS (EI): 347 (MH+).

Workup

  1. customto go to room temperature
  2. customThe reaction mixture was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-4793a91f1c2f4b9ca01a0d22c882c708
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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