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

tert-butyl N-(4-aminobutyl)carbamate → N-[4-(benzhydryl-amino)-butyl]-carbamic acid tert-butyl ester

HRID 2251949
Notes
Print preview

Reaction equation

HRID 2251949 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[K+].[CH:16](Br)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 4875Potassium IodideHCID 236603Bromodiphenylmethane

Product 1

HCID 53775424N-[4-(benzhydryl-amino)-butyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5.0 g (26.6 mmol) N-(tert-butoxycarbonyl)-1,4-diaminobutane 5.5 g (39.8 mmol) potassium carbonate and 0.9 g (5.3 mmol) potassium iodide are placed in 50 ml DMF and 6.6 g (26.6 mmol) benzhydryl bromide are added dropwise at RT. The mixture is stirred for 12 hours at 70° C. and the suspension is filtered after cooling and the filtrate is concentrated under vacuum. The residue is taken up in 200 ml chloroform and washed with 100 ml water. The organic phase is dried over sodium sulfate and, subsequently, the solvent is removed under vacuum. The accumulated crude product is further processed without further purification: Yield 10.8 g.

Workup

  1. filtrationthe suspension is filtered
  2. temperatureafter cooling
  3. concentrationthe filtrate is concentrated under vacuum
  4. washwashed with 100 ml water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customsubsequently, the solvent is removed under vacuum
  7. customis further processed without further purification

Sources & evidence

ORD record
ord-7a24c81354fb4ad39b75757daf1225e2
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07320993B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes