Triethylamine → 1-(t-Butyloxycarbonyl)-4-(4-morpholinecarbonyl)-1,4-diazepane

HRID 1003990Notes

Reaction equation

HRID 1003990 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:28]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 155382851-(t-Butyloxycarbonyl)-4-(4-morpholinecarbonyl)-1,4-diazepaneYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-(t-butyloxycarbonyl)-1,4-diazepane (92.0 g, 0.46 mol) and triethylamine (96.0 ml, 69.7 g, 0.69 mol) in dichloromethane (500 ml) at 0° C. was treated dropwise with a solution of 4-morpholinecarbonyl chloride (64.0 ml, 82.0 g, 0.55 mol) in dichloromethane (100 ml) and the reaction was stirred at room temperature under nitrogen for 18 hours. The reaction mixture was then diluted with dichloromethane (400 ml) and washed with 2N citric acid (3×400 ml), saturated brine (1×500 ml), dried over MgSO4 and evaporated to give the subtitle compound as an off-white solid (141.7 g, 98%). Rf 0.80 (0.880 aqueous ammonia:methanol:dichloromethane 1:10:90, v/v). MS m/z 314 (MH)+. Found: C,57.50; H,8.69; N,13.41; C15H27N3O4 requires C, 57.50; H, 8.69; N,13.41%.

Workup

  1. washwashed with 2N citric acid (3×400 ml), saturated brine (1×500 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-46ff98b306ef40b6a385b366f0145213
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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