Water → 2-Benzyloxymethyl-2-methyl-propane-1,3-diamine

HRID 12505Notes

Reaction equation

HRID 12505 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][CH2:15][C:16]([CH3:21])([C:19]#[N:20])[C:17]#[N:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C>[CH2:7]([O:14][CH2:15][C:16]([CH3:21])([CH2:19][NH2:20])[CH2:17][NH2:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59339437HCID 59339437, compound

Product 1

HCID 149593462-Benzyloxymethyl-2-methyl-propane-1,3-diamineYield 92.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

LiAlH4 (3.22 g; 84.84 mmol; 3.0 equiv.) was suspended in 30 mL dry diethylether and cooled with an ice bath. A solution of 2-Benzyloxymethyl-2-methyl-malononitrile (5.72 g; 28.28 mmol; 1.0 equiv.) in 20 mL dry diethylether was added dropwise. The suspension was stirred at room temperature for 4 hours, and subsequently cooled with an ice bath. To this was added 3.22 mL H2O, 6.44 mL 2 M NaOH and 3.22 mL H2O. The precipitate was filtered off and washed with ether. The filtrate was concentrated under reduced pressure to yield 5.47 g (84%) of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 0.84 (s, 3H), 2.59-2.69 (m, 4H) 3.29 (s, 2H), 4.49 (s, 2H), 7.24-7.39 (m, 5H).

Workup

  1. temperaturecooled with an ice bath
  2. temperaturesubsequently cooled with an ice bath
  3. filtrationThe precipitate was filtered off
  4. washwashed with ether
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bddcae2aae8a4f21aa0a7311799b508a
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Reaction notes

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