Methylamine → HCID 13809007, compound

HRID 1092365Notes

Reaction equation

HRID 1092365 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][NH2:13].[C-:14]#[N:15].[Na+]>CCOCC.O>[CH2:1]([O:8][CH2:9][CH:10]([NH:15][CH3:14])[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8929Sodium CyanideHCID 108989(Phenylmethoxy)acetaldehyde

Product 1

HCID 13809007HCID 13809007, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of known benzyloxy-acetaldehyde (10 g) in 25 mL ether, was added to an aqueous solution of methylamine (5.16 g of a 40% solution in water) at 0° C. followed by addition of NaCN (6.4 g dissolved in 10 mL water). The reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC and after completion, the ether layer was separated. The aqueous layer was extracted with 2×30 mL ethyl acetate and the combined organic layers were then dried over sodium sulfate, filtered and the volatiles where then concentrated to afford the crude product which was purified by column chromatography using basic alumina to give 3-benzyloxy-2-methylamino-propionitrile (5.0 g) as a dark brown oil.

Workup

  1. customafter completion, the ether layer was separated
  2. extractionThe aqueous layer was extracted with 2×30 mL ethyl acetate
  3. dry with materialthe combined organic layers were then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe volatiles where then concentrated
  6. customto afford the crude product which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8e8bee58bf1d4edd8673e6ff1a787712
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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