tert-butyl N-(4-aminobutyl)carbamate → 558446-23-4

HRID 628668Notes

Reaction equation

HRID 628668 reaction equation
[N:1]1[C:10]2[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].[BH4-].[Na+]>C(O)C.C(O)(=O)C>[N:1]1[C:10]2[CH:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 4311764Sodium borohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-one

Product 1

HCID 42609132558446-23-4

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6,7-dihydroquinolin-8(5H)-one (2.0 g, 13.6 mmol) in ethanol (15 mL) was added concentrated acetic acid (5 drops), tert-butyl 4-aminobutylcarbamate (2.7 g, 14.3 mmol) and 4 Å molecular sieves. The reaction mixture was heated at 150° C. in microwave reactor for 10 min. The mixture was cooled to room temperature and NaBH4 (0.8 g, 20.4 mmol) was added all at once. The crude reaction mixture was absorbed onto silica gel and the product purified by silica gel chromatography (0% to 10% methanol/CH2Cl2) to afford the desired product: ESI+ MS: m/z (rel intensity) 320.2 (100, [M+H]+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe crude reaction mixture
  3. customwas absorbed onto silica gel
  4. customthe product purified by silica gel chromatography (0% to 10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-3cf29a4ea91c4159998dc3b7445900e6
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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