Formaldehyde → 4-Chloro-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzeneethanamine

HRID 49974

Reaction equation

HRID 49974 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][CH:3]=1.[CH2:16]=O.CO.[C:20]([O-:23])([O-])=O.[K+].[K+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:16][O:23][CH3:20])[CH2:11][Si:12]([CH3:14])([CH3:13])[CH3:15])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 213010084-Chloro-N-[(trimethylsilyl)methyl]benzeneethanamine

Product 1

HCID 213010074-Chloro-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzeneethanamineYield 307%

Conditions

Temperature
0 °C

Procedure

The compound of formula (P14), in which n=2 and R″ is chloro, was prepared from 4-chloro-N-[(trimethylsilyl)methyl]benzeneethanamine (5.17 g, 21.38 mmol) (Preparation 11), added dropwise to ice-cooled aqueous formaldehyde (37% w/v, 2.3 g, 28.34 mmol). After 10 min., MeOH (3 mL, 74 mmol) was added and the mixture stirred at 0° C. for 3 h. Anhydrous K2CO3 (1 g) was then added and the mixture stirred for 30 min at 0° C. The layers were separated and the aqueous phase extracted with τ-Bu methyl ether. The combined organic layers were dried over MgSO4 and concentrated to yield the titled compound as a pale yellow oil (6.35 g). 1H NMR (CDCl3): 7.21 (2H, d, J=8.4 Hz), 7.09 (2H, d, J=8.4 Hz), 4.03 (2H, s), 3.21 (3H, s), 2.8-2.9 (2H, m), 2.65-2.8 (2H, m), 2.22 (2H, s), 0.03 (9H, s).

Workup

  1. additionadded dropwise to ice-
  2. stirringthe mixture stirred for 30 min at 0° C
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with τ-Bu methyl ether
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0c259f7023a74777bc8a1e525b72263c
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Linked notes

Loading…