Acetic Acid → N-(3-phenoxyphenyl)[[3-(1,1-dimethylethoxy)phenyl]methyl]amine

HRID 1017031Notes

Reaction equation

HRID 1017031 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[O:14]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[O:14]([C:21]1[CH:22]=[C:23]([NH:24][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:7]=2)[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 771353-PhenoxyanilineHCID 5049666Sodium triacetoxyborohydrideHCID 157122243-Tert-butoxybenzaldehyde

Product 1

HCID 10936948N-(3-phenoxyphenyl)[[3-(1,1-dimethylethoxy)phenyl]methyl]amineYield 41.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

EX-654B) The 3-t-butoxybenzaldehyde (0.585 g, 3.27 mmol) product from EX-654A and 3-phenoxyaniline (0.595 g, 3.21 mmol) were combined in 50 mL of THF, then solid NaBH(OAc)3 (0.860 g, 4.06 mmol) was added, and the mixture was stirred until uniform. Acetic acid (0.2 g, 3.33 mmol) was added, and the mixture was stirred at room temperature for 4 h, then quenched with 5% aq. NaHCO3. The aqueous layer was separated and extracted twice with ether. The combined ether layers were washed with water and brine, dried over MgSO4, filtered, and evaporated to give 1.29 g (115%) of crude product as a brown oil. Chromatography on silica gel eluting with 0-10% ethyl acetate in hexane gave 464 mg (40%) of the desired N-(3-phenoxyphenyl)[[3-(1,1-dimethyl-ethoxy)phenyl]methyl]amine product as a colorless oil, pure by TLC. MS m/z=347 [M+].

Workup

  1. stirringthe mixture was stirred at room temperature for 4 h
  2. customquenched with 5% aq. NaHCO3
  3. customThe aqueous layer was separated
  4. extractionextracted twice with ether
  5. washThe combined ether layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give 1.29 g (115%) of crude product as a brown oil

Sources & evidence

ORD record
ord-da176ce507d548d489cd13a5020de814
Source dataset
uspto-grants-2002_11
Patent number
US06476057B1

Reaction notes

Loading…