Triethylamine → N-(1-cyclopropyl piperidine-4-carbonyl)-N'-(5-amino-6-chloro chroman-8-carbonyl) hydrazine

HRID 1523730Notes

Reaction equation

HRID 1523730 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]([NH:15][NH2:16])=[O:14])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][O:7]2.C(N(CC)CC)C.[CH:24]1([N:27]2[CH2:32][CH2:31][CH:30]([C:33](Cl)=[O:34])[CH2:29][CH2:28]2)[CH2:26][CH2:25]1>ClCCl.O>[CH:24]1([N:27]2[CH2:28][CH2:29][CH:30]([C:33]([NH:16][NH:15][C:13]([C:9]3[CH:10]=[C:11]([Cl:12])[C:2]([NH2:1])=[C:3]4[C:8]=3[O:7][CH2:6][CH2:5][CH2:4]4)=[O:14])=[O:34])[CH2:31][CH2:32]2)[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 867249091-Cyclopropylpiperidine-4-carbonyl chlorideHCID 867249165-Amino-6-chloro-chroman-8-carboxylic acid hydrazide

Product 1

HCID 86724915N-(1-cyclopropyl piperidine-4-carbonyl)-N'-(5-amino-6-chloro chroman-8-carbonyl) hydrazineYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-amino-6-chloro chroman-8-carboxylic acid hydrazide (8.0 grams, 33.1 mmol, obtained in preparation 1) in dichloromethane (200 mL) cooled at 0° C., was added triethylamine (13.9 mL, 99.9 mmol) and a solution of 1-cyclopropylpiperidine-4-carbonyl chloride (11.0 grams) in dichloromethane (200 mL). The reaction mixture was warmed to room temperature and stirred for 16 hours before diluting it with water (160 mL). The two layers were separated, the organic layer was dried over anhydrous sodium sulphate and the volatiles were removed under reduced pressure to obtain the title compound (10.5 grams).

Workup

  1. customThe two layers were separated
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-3bdfdfdec219413d9b0eec5a5bcc5a1d
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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