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Aluminium lithium hydride → N1,N1-diethyl-2,2-diphenylpropane-1,3-diamine

HRID 1685308
Notes
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Reaction equation

HRID 1685308 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]#[N:7])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][NH2:7])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 467073363-(Diethylamino)-2,2-diphenylpropanenitrile

Product 1

HCID 59200426N1,N1-diethyl-2,2-diphenylpropane-1,3-diamineYield 80.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(diethylamino)-2,2-diphenylpropanenitrile (0.627 g, 2.25 mmol) in diethyl ether (5 mL) was slowly added to a suspension of lithium aluminum hydride (0.171 g, 4.50 mmol) in diethyl ether (5 mL) at 0° C. The resulting slurry was stirred at 0° C. for 1.5 hours. The reaction was then quenched by adding sodium sulphate decahydrate and stirring for 30 minutes. The reaction was then diluted with ethyl acetate and celite was added. The suspension was filtered and the filtrate was concentrated to dryness to give the title material (0.511 g, 80%) as an oil. LC/MS (M+H)+: 283. HPLC ret. time (Condition B): 1.602 min. 1H NMR (400 MHz, CDCl3) δ ppm: 0.81 (6H, t, J=7.07 Hz), 2.19 (4H, q, J=7.07 Hz), 3.18 (2H, s), 3.51 (2H, s) 7.16-7.20 (6H, m) 7.24-7.32 (4H, m).

Workup

  1. customThe reaction was then quenched
  2. additionby adding sodium sulphate decahydrate
  3. stirringstirring for 30 minutes
  4. additionThe reaction was then diluted with ethyl acetate and celite
  5. additionwas added
  6. filtrationThe suspension was filtered
  7. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a670714e3091433ca50bebe99cd351c2
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148400B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes