Tert-butyl N-[(4-cyanophenyl)methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate → 4-(Aminomethyl)benzonitrile hydrochloride

HRID 1071953Notes

Reaction equation

HRID 1071953 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.O1CCOCC1.[ClH:31]>>[ClH:31].[C:16]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1)#[N:8]

Participants

3

Reactant 2

HCID 3683768Tert-butyl N-[(4-cyanophenyl)methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 99422504-(Aminomethyl)benzonitrile hydrochloride

Procedure

4-cyanobenzylamine hydrochloride (EX-59A) was prepared from 10 g (0.030 moles) of 4{N,N-bis-(tert-butoxycarbonyl)aminomethyl}benzonitrile, prepared following Synthetic Communication, 28(23), 4419-4429 (1998), by stirring it in 4N HCl Dioxane (75 ml). After 3 h, the solution was concentraed in vacuo and triturated with ether. The solid was collected by filtration and vacuum dried to yield 5 g (98%) of EX-59A as a white solid: 1H NMR (DMSO) d 8.68 (br s, 2H), 7.84 (m, 2H), 7.67 (m, 2H), 4.06 (s, 2H); HRMS (EI) calcd for C8H8N2 133.0766, found 133.0807

Workup

  1. customprepared
  2. customtriturated with ether
  3. filtrationThe solid was collected by filtration and vacuum
  4. customdried
  5. customto yield 5 g (98%) of EX-59A as a white solid

Sources & evidence

ORD record
ord-a4b36b65f7b4408092c9579228679e03
Source dataset
uspto-grants-2005_06
Patent number
US06908919B2

Reaction notes

Loading…