N-benzylpropane-1,3-diamine → Tert-Butyl N-[3-(Benzylamino)Propyl]Carbamate(WXC03618)

HRID 2393727Notes

Reaction equation

HRID 2393727 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([O:17][C:18](ON=C(C1C=CC=CC=1)C#N)=[O:19])([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[C:13]([O:17][C:18]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 83811N-benzylpropane-1,3-diamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2×

Product 1

HCID 10244573Tert-Butyl N-[3-(Benzylamino)Propyl]Carbamate(WXC03618)Yield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(3-aminopropyl)benzylamine (38 g, 231.71 mmoles) in dry tetrahydrofuran (300 mL) was cooled to 5° C. in an ice-alcohol bath. To this cold stirred solution 2-[[(tert-butyoxycarbonyl)oxy]imino]-2-phenylacetonitrile (BOC-ON) (56.58 g, 230 mmoles) in dry tetrahydrofuran (300 mL) was added slowly during a 6 hour period. After the addition of BOC-ON, the reaction mixture was stirred at room temperature under argon for an additional 6 hours. The reaction mixture was evaporated to dryness and the residue was dissolved in ether (750 mL). The ether extract was washed with 5% sodium hydroxide solution (4×100 mL), dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was purified by flash column using a chromatograpay over a silica dichloromethane→methanol gradient. The pure fractions were pooled together and evaporated to give 49.5 g (81%) of product as oil: 1H nmr (deuteriochloroform): δ 1.42 (s, 9H, t-Boc), 1.65 (m, 2H, CH2CH2CH2), 2.70 (t, 2H, CH2 NHCH2), 3.20 (m, 2H, BocNHCH2), 3.78 (s, 2H, ArCH2), 5.32 (br s, 1H, BocNH), 7.30 (m, 5H, ArH).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in ether (750 mL)
  3. extractionThe ether extract
  4. washwas washed with 5% sodium hydroxide solution (4×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by flash column
  8. customevaporated

Sources & evidence

ORD record
ord-c8ccfbe2b50b4d9e9fef9e43d11d402c
Source dataset
uspto-grants-1998_09
Patent number
US05808027

Reaction notes

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