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

HRID 1840050

Reaction equation

HRID 1840050 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

The 3-t-butoxybenzaldehyde (0.585 g, 3.27 nmmol) 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-b5155c5a982d49159cef8a01837a222e
Source dataset
uspto-grants-2004_01
Patent number
US06677375B2

Linked notes

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