Acetic Acid → (2-(1-(4-Cyanophenyl)piperidin-4-ylamino)ethyl)carbamic acid tert-butyl ester

HRID 842786Notes

Reaction equation

HRID 842786 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[NH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:22]([O:21][C:20](=[O:26])[NH:19][CH2:18][CH2:17][NH:16][CH:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:10][CH2:11]1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 110198874-(4-Oxopiperidin-1-yl)benzonitrile

Product 1

HCID 54428198(2-(1-(4-Cyanophenyl)piperidin-4-ylamino)ethyl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 35 (415 mg, 2.07 mmol), 1 (343 mg, 2.14 mmol), and acetic acid (629 mg, 10.48 mmol) in methanol (10 mL) was treated with sodium cyanoborohydride (140 mg, 2.23 mmol) at room temperature. The resulting mixture was stirred at room temperature (3 h). The solvent was removed in vacuo. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (36).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-381f7ee5cfdc425894689bb1db906fbf
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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