HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzylamine → (+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-[(phenylmethyl)amino]benzeneacetamide

HRID 465645
Notes
Print preview

Reaction equation

HRID 465645 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:23])[CH:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:23])[CH:15]([NH:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 19874874(+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-bromobenzeneacetamide

Product 1

HCID 19874931(+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-[(phenylmethyl)amino]benzeneacetamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (±)-N-[2,6-bis(1-Methylethyl)phenyl]-α-bromobenzeneacetamide (4.3 g, 12 mmol), benzylamine (1.8 g, 18 mmol), and triethylamine (8.0 mL, 57 mmol) in toluene was refluxed (96 hours) then cooled and concentrated in vacuo. The residue was taken up in ethyl acetate (300 mL), washed with water (2×100 mL), with saturated aqueous sodium bicarbonate (1×100 mL), with brine (1×100 mL), then dried (MgSO4) and concentrated to a solid. The solid was recrystallized from ethyl acetate/hexane to yield 3.35 g (72.8%) of the title compound as a white solid, mp 134°-137° C.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated in vacuo
  3. washwashed with water (2×100 mL), with saturated aqueous sodium bicarbonate (1×100 mL), with brine (1×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a solid
  6. customThe solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d32a1480c5094961b7ce00a504365f85
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05153226

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes