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Diisopropylethylamine → 1-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-one

HRID 1907272
Notes
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Reaction equation

HRID 1907272 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH2:17])[CH3:11])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOCC>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:17][C:34]2=[O:36])[CH3:11])=[CH:8][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 68630318N1-((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochloride

Product 1

HCID 582000411-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-oneYield 25%

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of N1—((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochloride (19.5 mg, 0.046 mmol) and i-Pr2NEt (0.10 mL, 0.56 mmol) in CH2Cl2 (8 mL) was cooled in an ice bath and solid triphosgene (4.6 mg, 0.015 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was diluted with ether (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent left a residue (17.5 mg) which was purified by preparative HPLC to afford 1-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-one (1.4 mg, 8%). LC-MS (3 min) tR=2.05 min, m/z=375, 373.

Workup

  1. washwashed with 5% aq HCl (20 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. waitleft a residue (17.5 mg) which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f2f7e3249dc045fbb590d86dd9fd973b
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598160B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes