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Morpholine → HCID 18348512, compound

HRID 2268505
Notes
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Reaction equation

HRID 2268505 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1)[CH2:7]2.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>C1COCC1.O.C(N(CC)CC)C>[CH3:17][O:16][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:28])=[CH:25][CH:24]=1)[CH2:5]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18348557HCID 18348557, compound

Product 1

HCID 18348512HCID 18348512, compound

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8471TriethylamineSolvent

Procedure

A mixture of 4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoic acid (3.50 g), morpholine (1.42 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.12 g), 1-hydroxybenzotriazole monohydrate (2.45 g), and triethylamine (2.30 ml) in THF (70 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride and dried. Removal of the solvent in vacuo gave the entitled compound (4.00 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  3. customdried
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-628625b5166b4faeaf51ab7e4c1323fd
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes