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

Participants

Role	Name	HCID	Charge
Reactant	8-Benzyl-8-azabicyclo(3.2.1)octan-3-one	HCID 119846	—
Reactant	Sodium cyanoborohydride	HCID 5003444	—
Reactant	(+,-)-Bromoacetyl-2-(3,4-dichlorophenyl)-4-(3,5-dimethylbenzoyl)piperazine	HCID 10277726	—
Reactant	(+,-)-2-(3,4-Dichlorophenyl)-4-[3,5-dimethylbenzoyl]-1-[[[3-methyl-1-(phenylmethyl)-4-piperidinyl]amino]acetyl]piperazine	HCID 15887547	—
Solvent	Water	HCID 962	—
Product	Ammonia	HCID 222	—
Product	2-(3,4-Dichlorophenyl)-4-(3,5-dimethylbenzoyl)-1-[[[8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]amino]acetyl]piperazine	HCID 44214921	—

Reaction Steps

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.

Provenance & Evidence

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