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8-Benzyl-8-azabicyclo(3.2.1)octan-3-one → Ammonia

HRID 362544
Notes
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Reaction equation

HRID 362544 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][N:13]([C:15](=[O:24])[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=3)[CH2:12][CH2:11][N:10]2[C:25](=[O:42])[CH2:26][NH:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:30][CH:29]2[CH3:41])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:44]C(N1CCN(C(=O)C2C=C(C)C=C(C)C=2)CC1C1C=CC(Cl)=C(Cl)C=1)=O.C(N1C2CCC1CC(=O)C2)C1C=CC=CC=1.[BH3-]C#N.[Na+]>O>[NH3:10].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][N:13]([C:15](=[O:24])[C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=3)[CH2:12][CH2:11][N:10]2[C:25](=[O:42])[CH2:26][NH:27][CH:28]2[CH2:44][CH:30]3[N:31]([CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:32]([CH2:41][CH2:29]3)[CH2:33]2)[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-oneHCID 5003444Sodium cyanoborohydrideHCID 10277726(+,-)-Bromoacetyl-2-(3,4-dichlorophenyl)-4-(3,5-dimethylbenzoyl)piperazineHCID 15887547(+,-)-2-(3,4-Dichlorophenyl)-4-[3,5-dimethylbenzoyl]-1-[[[3-methyl-1-(phenylmethyl)-4-piperidinyl]amino]acetyl]piperazine

Product 2

HCID 222Ammonia
HCID 442149212-(3,4-Dichlorophenyl)-4-(3,5-dimethylbenzoyl)-1-[[[8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]amino]acetyl]piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By an analogous method to that described in Example 16, the product from Example 16, compound 3 (185 mg, 0.44 mmol) was combined with 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (97 mg, 0.45 mmol) and Ti(O-i Pr)4 (105 mL, 0.50 mmol) and left stirring for 1 h. To the thick reaction mixture was added NaBH3CN (59.5 mg, 0.95 mmol) and the mixture was stirred overnight. To the reaction mixture was added H2O (1 mL) and it was filtered. The filtrate was washed with EtOH, concentrated and purified by silica gel chromatography, eluting with 30:1:0.1 to 15:1:0.1 CH2Cl2 --MeOH--NH3 aq. to give the title product as a white foam. HRMS (FAB, M+H+); m/e calc'd [C35H41Cl2N4O2 ]+ : 619.2607, found 619.2594.

Workup

  1. waitleft
  2. stirringthe mixture was stirred overnight
  3. filtrationwas filtered
  4. washThe filtrate was washed with EtOH
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography
  7. washeluting with 30:1:0.1 to 15:1:0.1 CH2Cl2

Sources & evidence

ORD record
ord-f4ac5dc9cb654804b86208e3328ee031
Source dataset
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05869488

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes