Hydrochloric Acid → N1-((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochloride

HRID 1907271Notes

Reaction equation

HRID 1907271 reaction equation
[NH2:1][CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][CH2:5][N:6]([C@H:14]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)[CH3:15])C(=O)OC(C)(C)C.[ClH:29]>C(Cl)Cl.O1CCOCC1>[ClH:29].[ClH:29].[Br:22][C:19]1[CH:18]=[CH:17][C:16]([C@@H:14]([NH:6][CH2:5][CH2:4][CH2:3][CH:2]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH2:1])[CH3:15])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67043294tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamate

Product 1

HCID 68630318N1-((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochlorideYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamate (179 mg, 0.40 mmol) in CH2Cl2 (5 mL) at rt was added 4 M HCl in dioxane (5 mL). The mixture was stirred for 1 h and concentrated to afford N1-((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochloride (162 mg, 96%). LC-MS Method 1 tR=0.92 min, m/z=349, 347.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-cd5fe90a202f4d2c9ef2eadd9e97cb9a
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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