Ammonia → 5-Phthalimido-1-pentanol

HRID 2395092Notes

Reaction equation

HRID 2395092 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C(N1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])(OCC)=O.C(#N)C.N>C1C=CC=CC=1.C(Cl)(Cl)Cl>[C:14]1(=[O:23])[N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7])[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6342AcetonitrileHCID 31187N-CarbethoxyphthalimideHCID 756345-Aminopentan-1-ol

Product 1

HCID 5948445-Phthalimido-1-pentanolYield 84%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

A solution of 5-amino-1-pentanol (5.00 g, 48.5 mmol) in benzene (150 ml) was treated with N-carboethoxyphthalimide (11.0 g, 50.2 mmol) and stirred at room temperature for 5 h. Concentration in vacuo and flash chromatography (25% ethyl acetate/petroleum ether) yielded III-33 (9.6 mg, 84% yield) as a clear, colorless oil: UV (9.65×10-4M, acetonitrile) λmax 292.0 (ε212), 242.4 (226) nm; IR (CHCl3) 3460 (br), 2940 (s), 2860 (s), 1770 (s), 1710 (s), 1610 (s), 1470 (s), 1440 (s), 1400 (s), 1370 (s), 1190 (m), 1170 (m), 1130 (m), 1050 (s), 960 (m), 890 (m), 875 (m), 790 (m), 720 (s) cm-1 ; 1H NMR (500 MHz, CDCl3) δ7.72-7.70 (m, 2 H), 3.69 (t, J=7.2 Hz, 1 H), 3.64 (t, J=6.5 Hz, 1 H), 2.17 (br s, 1 H), 1.74-1.59 (m, 2 H), 1.46-1.40 (m, 1 H); 13C NMR (125 MHz, CDCl3) δ169.39, 133.78, 131.96, 123.05, 62.34, 37.74, 32.03, 28.22, 22.93; high resolution mass spectrum (Cl, NH3) m/z 234.1108 [(M+H)+ ; calcd for C13 H15NO3 : 234.1129].

Workup

  1. concentrationConcentration in vacuo and flash chromatography (25% ethyl acetate/petroleum ether)
  2. customyielded III-33 (9.6 mg, 84% yield) as a clear, colorless oil

Sources & evidence

ORD record
ord-22bf1509636e4c02b613d0df49bc3537
Source dataset
uspto-grants-1998_09
Patent number
US05811512

Reaction notes

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