Silane, (chloromethyl)trimethyl- → HCID 68837258, compound

HRID 1454351Notes

Reaction equation

HRID 1454351 reaction equation
[CH2:1]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Cl[CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>CS(C)=O>[CH3:19][Si:20]([CH2:23][NH:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:17][CH:16]=1)([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 75361Silane, (chloromethyl)trimethyl-HCID 23117394HCID 23117394, compound

Product 1

HCID 68837258HCID 68837258, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1.3 g (6 mmol) of 4-(nonyl)benzylamine (from Step A) and 700 mg (6 mmol) of chloromethyltrimethylsilane in 5 mL of DMSO was stirred at 90° C. for 3 h, then at rt for 16 h. The mixture was partitioned between MTBE and 1N NaOH. The organic layer was separated, washed with sat'd NaCl, dried and concentrated. Flash chromatography using 9:1 v/v hexane/EtOAc as the eluant afforded 700 mg of N-(trimethylsilylmethyl)-4-(nonyl)benzylamine.

Workup

  1. customThe mixture was partitioned between MTBE and 1N NaOH
  2. customThe organic layer was separated
  3. washwashed with sat'd NaCl
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b33375ab10cb407e8c29304b435df1fd
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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