Phosgene → HCID 86615684, compound

HRID 643581Notes

Reaction equation

HRID 643581 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[NH:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[NH:13][C:12]2=[O:22])[CH2:7][CH2:6]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[O:22]=[C:12]1[N:11]([CH:8]2[CH2:9][CH2:10][N:5]([C:1]([Cl:4])=[O:2])[CH2:6][CH2:7]2)[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Product 1

HCID 86615684HCID 86615684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6 g (12.1 mmol) phosgene (20 percent by weight in toluene) were added to a solution of 2.5 g (10.2 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 2.6 mL (14.9 mmol) ethyldiisopropylamine in 75 mL DCM cooled to 0° C. and the reaction mixture was stirred for 30 min at this temperature. The mixture was allowed to warm up to RT, evaporated down i.vac. to approx. 50 mL and filtered through silica gel, this was washed with 200 mL DCM/EtOAc (1:1) and the combined organic filtrates were again evaporated down i.vac. The residue was stirred with DIPE, suction filtered and dried i.vac.

Workup

  1. temperatureto warm up to RT
  2. customevaporated down i.vac
  3. filtrationto approx. 50 mL and filtered through silica gel
  4. washthis was washed with 200 mL DCM/EtOAc (1:1)
  5. customthe combined organic filtrates were again evaporated down i.vac
  6. stirringThe residue was stirred with DIPE, suction
  7. filtrationfiltered
  8. customdried i.vac

Sources & evidence

ORD record
ord-30f4bcbe528a42c3be76bf6990f45d43
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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