2-(Adamantan-1-yl)-N-methylethan-1-amine → HCID 21974209, compound

HRID 2075907Notes

Reaction equation

HRID 2075907 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[C:13]12([CH2:23][CH2:24][NH:25][CH3:26])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.C(N(C(C)C)CC)(C)C.[CH3:36][NH:37][CH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=1>ClCCl.C(OCC)C>[C:13]12([CH2:23][CH2:24][N:25]([CH3:26])[C:5]([N:37]([CH3:36])[CH2:38][CH2:39][CH2:40][C:41]3[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=3)=[O:11])[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2

Participants

7

Reactant 4

HCID 359962-(Adamantan-1-yl)-N-methylethan-1-amineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 21974070N-Methyl-3-(pyridin-4-yl)propan-1-amine

Product 1

HCID 21974209HCID 21974209, compoundYield 141.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of triphosgene (190 mg, 0.640 mmol) in dichloromethane (6.0 ml) was stirred at room temperature under a nitrogen atmosphere. A solution of 2-(1-adamantyl)-N-methylethylamine (Intermediate No. 3-1) (330 mg, 1.71 mmol) and diisopropylethylamine (0.357 ml, 2.05 mmol) in dichloromethane (6.0 ml) was added dropwise thereto over 17 minutes. After eight minutes, a solution of N-methyl-3-(4-pyridyl)propylamine (Intermediate No. 3-3) (264 mg, 1.78 mmol) and diisopropylethylamine (0.357 ml, 2.05 mmol) in dichloromethane (5.1 ml) was added to the mixture at a stretch, and the whole was stirred for 20 hours. The reaction mixture was diluted with diethyl ether (40 ml), the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (40 ml) twice and a saturated aqueous sodium chloride solution (40 ml) successively, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 335 mg (54%) of the titled compound.

Workup

  1. waitAfter eight minutes
  2. washthe whole was washed with a saturated aqueous sodium hydrogencarbonate solution (40 ml) twice
  3. dry with materiala saturated aqueous sodium chloride solution (40 ml) successively, and the organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b74c24f4aee8402686e3d33d80ff1ca1
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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