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1,2-Dichloroethane → HCID 59173048, compound

HRID 45177
Notes
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Reaction equation

HRID 45177 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH:16]([C:17]([OH:19])=O)[CH:15]2[O:20][CH:12]1[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1([CH2:27][CH2:28][OH:29])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CO.C(Cl)Cl>[CH2:1]([O:8][C:9]([CH:11]1[CH:16]([C:17]([N:24]2[CH2:25][CH2:26][N:21]([CH2:27][CH2:28][OH:29])[CH2:22][CH2:23]2)=[O:19])[CH:15]2[O:20][CH:12]1[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 76771-(2-Hydroxyethyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21127829HCID 21127829, compound

Product 1

HCID 59173048HCID 59173048, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of compound 10 (3.00 g, 11.6 mmol) in CH2Cl2 at 0° C. (60 mL) was added piperazine-1-ethanol (11) (1.82 g, 14.0 mmol), EDC (3.12 g, 16.3 mmol), HOBt (0.20 g) and DIPEA (5.8 mL, 34.9 mmol). The mixture was allowed to warm to RT over 16 h. TLC (5% MeOH/CH2Cl2) showed no starting material. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with water (2×40 mL) and dried. Evaporation of organic layer gave a residue. The residue was triturated with diisopropyl ether (20 mL) to get 3-[4-(2-hydroxy-ethyl)-piperazine-1-carbonyl]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester (12) as a white solid. Yield: 3.24 g (72%). Mp 72-75 C. 1H NMR (300 MHz, CDCl3) δ 1.42-1.56 (m, 2H); 1.76-1.82 (m, 2H); 2.02 (s, 2H); 2.29-2.51 (m, 4H); 2.90 (d, J=6.4 Hz, 1H); 3.08 (d, J=6.1 Hz, 1H); 3.18-3.24 (m, 2H); 3.41 (bs, 1H); 3.60 (t, J=2.3 Hz, 2H); 3.69 (bs, 1H); 4.90 (dd, J=6.8 Hz, 2.3 Hz, 2H); 5.08 (s, 2H); 7.28-7.40 (m, 5H).

Workup

  1. washwashed with water (2×40 mL)
  2. customdried
  3. customEvaporation of organic layer
  4. customgave a residue
  5. customThe residue was triturated with diisopropyl ether (20 mL)

Sources & evidence

ORD record
ord-ccd1a503b4e54b72a9bf1f0908587715
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541458B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes