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

HRID 1243356Notes

Reaction equation

HRID 1243356 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 concentrated 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. concentrationthe solution was concentrated in vacuo
  3. customtriturated with ether
  4. filtrationThe solid was collected by filtration and vacuum
  5. customdried
  6. customto yield 5 g (98%) of EX-59A as a white solid

Sources & evidence

ORD record
ord-be95f0885f73452bae4d6d1b75957a49
Source dataset
uspto-grants-2006_10
Patent number
US07119094B1

Reaction notes

Loading…