Hydrochloric Acid → 1-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride

HRID 1003991Notes

Reaction equation

HRID 1003991 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>ClCCl.CO>[ClH:23].[N:17]1([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)=[O:16])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 155382851-(t-Butyloxycarbonyl)-4-(4-morpholinecarbonyl)-1,4-diazepane

Product 1

HCID 227070621-(4-Morpholinecarbonyl)-1,4-diazepane hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 1-(t-butyloxycarbonyl)-4-(4-morpholinecarbonyl)-1,4-diazepane (140.0 g, 0.44 mol) in dichloromethane:methanol (1:1, v/v, 600 ml) at 0° C. was saturated with hydrogen chloride gas and the reaction mixture was stirred at room temperature under nitrogen for 18 hours after which time the reaction mixture was evaporated under reduced pressure and slurried in ethyl acetate to give, after filtration, a white hygroscopic solid. This was further purified by slurrying in acetone, filtering, washing with diethyl ether and drying in vacuo at 60° C. to give the title compound as a colourless solid (99.0 g, 90%). Rf 0.41 (0.880 aqueous ammonia:methanol:dichloromethane 2:14:84, v/v). MS m/z 214 (MH)+. Found: C,47.50; H,8.10; N,16.55; C10H19N3O2HCl 0.2H2O requires C, 47.41; H, 8.12; N,16.59%.

Workup

  1. customat 0° C.
  2. customwas evaporated under reduced pressure
  3. customto give
  4. filtrationafter filtration
  5. customThis was further purified
  6. filtrationfiltering
  7. washwashing with diethyl ether
  8. customdrying in vacuo at 60° C.

Sources & evidence

ORD record
ord-66c41d554db841b6bd2c36a83ad5e92a
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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