Hydrogen Bromide → HCID 178419265, compound

HRID 1521742Notes

Reaction equation

HRID 1521742 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:3]=1.[BrH:17].[N:18]#[C:19][Br:20]>C(O)C.C(Cl)Cl.C(OCC)C>[BrH:20].[BrH:17].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[NH:9][C:19]([NH2:18])=[N:8][C:6]=2[CH:7]=1

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 10476Cyanogen BromideHCID 67235894HCID 67235894, compound

Product 1

HCID 178419265HCID 178419265, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-3-(morpholin-4-ylmethyl)benzene-1,2-diamine (458 mg, 1.9 mmol) in ethanol (5 mL) is added a 48% aqueous HBr solution (0.21 mL, 1.9 mmol) followed by a 3M solution of cyanogen bromide (0.95 mL, 2.8 mmol) in CH2Cl2. The reaction is stirred at room temperature for 4 h and is diluted with diethyl ether. The resulting solid is isolated by filtration to afford the title compound as the dihydrobromide salt (595 mg, 73%).

Workup

  1. customThe resulting solid is isolated by filtration

Sources & evidence

ORD record
ord-4da686639cc64cfdb6b0366091a39f0b
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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