1-(2-(1-Methylpyrrolidin-2-yl)ethyl)-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one → 7-Amino-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

HRID 1922441Notes

Reaction equation

HRID 1922441 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]2[CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=[CH:20][C:10]1=2>C(O)C.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:10]2[N:9]([CH2:8][CH2:7][CH:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]=2[CH:17]=1

Participants

4

Reactant 1

HCID 674928061-(2-(1-Methylpyrrolidin-2-yl)ethyl)-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Product 1

HCID 674926797-Amino-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2 (600 mg, 1.89 mmol) in dry ethanol (10 mL) was treated with Pd—C (˜0.06 g) and purged with hydrogen gas. The reaction mixture was stirred at room temperature under hydrogen atmosphere (balloon pressure) overnight (18 h). The mixture was filtered through a celite bed and washed with methanol (3×25 mL). The combined organic fractions were concentrated to give a brown residue. The product was purified by dry column chromatography (2 N NH3 in MeOH:CH2Cl2, 5:95) to give compound 3 (435 mg, 80%) as a colourless foam. 1H-NMR (DMSO-d6, 300 MHz) δ: 1.29-1.38 (m, 2H), 1.54-1.60 (m, 2H), 1.66-1.82 (m, 2H), 1.89-2.10 (m, 10H), 2.38-2.45 (m, 2H), 2.84-2.91 (m, 1H), 5.07 (brs, 2H), 6.36-6.52 (m, 2H), 6.85-6.98 (m, 1H).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe mixture was filtered through a celite bed
  3. washwashed with methanol (3×25 mL)
  4. concentrationThe combined organic fractions were concentrated
  5. customto give a brown residue
  6. customThe product was purified
  7. dry with materialby dry column chromatography (2 N NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-1e4925e598174c3eba74a8373990d7fd
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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