Benzhydrylamine → HCID 15113033, compound

HRID 2425528Notes

Reaction equation

HRID 2425528 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][Si:16]([CH2:19]Cl)([CH3:18])[CH3:17]>C(#N)C>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 15113033HCID 15113033, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of benzhydrylamine (25 g, 136.4 mmol) and trimethylsilylmethyl chloride (8.39 g, 68.4 mmol) in acetonitrile (105 ml) was refluxed overnight. Then the mixture was concentrated under vacuum at 70° C. with a rotary evaporator to remove all volatiles. The white residue was mixed with n-heptane (150 ml) and filtered over a glass filter. The salt residue was washed with n-heptane (2×25 ml). The combined heptane filtrates were concentrated under vacuum to give the crude product as a clear, slightly yellow oil (23 g; >100%). Purification by chromatography on silica gel (700 ml) eluting with n-heptane (2000 ml), followed by n-heptane:ethyl acetate (10:1) gave pure diphenyl-N-((trimethylsilyl)methyl)methanamine (5.5 g, 20.4 mmol; 30%).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThen the mixture was concentrated under vacuum at 70° C. with a rotary evaporator
  3. customto remove all volatiles
  4. additionThe white residue was mixed with n-heptane (150 ml)
  5. filtrationfiltered over a glass
  6. filtrationfilter
  7. washThe salt residue was washed with n-heptane (2×25 ml)
  8. concentrationThe combined heptane filtrates were concentrated under vacuum
  9. customto give the crude product as a clear, slightly yellow oil (23 g; >100%)
  10. customPurification by chromatography on silica gel (700 ml)
  11. washeluting with n-heptane (2000 ml)

Sources & evidence

ORD record
ord-2b34c23c52fa4ef38dde07cc3df49eb1
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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