Water → HCID 178419545, compound

HRID 415105Notes

Reaction equation

HRID 415105 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[NH2:22])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.O.[N:24]#[C:25][Br:26]>C(#N)C>[BrH:26].[NH2:24][C:25]1[NH:22][C:21]2[CH:20]=[CH:19][C:4]([O:5][CH:6]3[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]3)=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 59349514HCID 59349514, compound

Product 1

HCID 178419545HCID 178419545, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 4-(3,4-diaminophenoxy)piperidine-1-carboxylate (5.673 mmoles, 1.914 g, 1 equivalent) was dissolved in acetonitrile (20 ml) and water (20 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (5.67 mmoles, 0.721 g, 1.4 equivalents) 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 2.41 g of tert-butyl 4-(2-amino-1H-benzo[d]imidazol-5-yloxy)piperidine-1-carboxylate hydrobromide (yield: 100%) which was used directly in the next reaction without any further purification. 1H-NMR (400 MHz, DMSO-d6) δ 12.22 (br s, 2H), 8.39 (s, 2H), 7.22 (d, 1H), 6.91 (s, 1H), 7.83 (d, 1H), 4.50 (m, 1H), 3.61 (m, 2H), 2.19 (, 2H), 1.90 (m, 2H), 1.40 (s, 9H). MS (EI): 333 (MH+).

Workup

  1. customto go to room temperature

Sources & evidence

ORD record
ord-3d5f088cf28f4b83a0aa5920148d6cee
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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