Ammonia → 5-(Cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441674Notes

Reaction equation

N.[Li].C([N:10]1[C:23]2[C:18](=[CH:19][C:20]([CH2:24][CH:25]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:21][CH:22]=2)[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:11]1=[O:33])C1C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[CH:25]1([CH2:24][C:20]2[CH:19]=[C:18]3[C:12]4([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]4)[C:11](=[O:33])[NH:10][C:23]3=[CH:22][CH:21]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a magnetically stirred solution of liquid ammonia (10 mL) was added lithium (20 mg) at −78° C. under nitrogen atmosphere causing the solution to turn dark-blue. To the reaction mixture was then added a solution of 1-benzyl-5-(cyclooctyl-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.025 g, 0.06 mmol) in dry THF (2 mL). The reaction mixture was stirred −78° C. under nitrogen atmosphere for a few minutes, then ammonium chloride was added and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a foam.

Workup

stirringthe reaction mixture was stirred at room temperature for one hour
customThe reaction mixture was partitioned with water and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried with Na2SO4
filtrationfiltered
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-741b9802c2fa4a0ead88a081a94898b6
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655670B2

Reaction notes

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