Diisopropylethylamine → Benzyl-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amide

HRID 2407538Notes

Reaction equation

HRID 2407538 reaction equation
[CH2:1]([N:8]1[C:11]2([CH2:14][NH:13][CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[N:24]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:25]=[O:26]>ClCCl>[C:30]1([CH2:29][CH2:28][CH2:27][NH:24][C:25]([N:13]2[CH2:12][C:11]3([N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:9][CH2:10]3)[CH2:14]2)=[O:26])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 34276663-Phenylpropyl isocyanateHCID 569621441-Benzyl-1,6-diazaspiro[3.3]heptane

Product 1

HCID 71554979Benzyl-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amideYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-1,6-diaza-spiro[3.3]heptane (41 mg, 217 μmol) in dichloromethane (2 mL) was added diisopropyl-ethyl-amine (112 mg, 868 μmol)) followed by (3-isocyanato-propyl)-benzene (84 mg, 521 μmol) and the reaction mixture was allowed to stir at ambient temperature for 16 h. After complete consumption of starting material the reaction mixture was diluted with dichloromethane and was washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. Purification by HPLC afforded the title compound (9 mg, 12%) as an off-white solid. MS m/e: 350 (M+H)+.

Workup

  1. customAfter complete consumption of starting material the reaction mixture
  2. additionwas diluted with dichloromethane
  3. washwas washed successively with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-af2afb0f070048df92e6f5e3aa7c3b69
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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