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1,2-Dichloroethane → HCID 59173048, compound

HRID 1516248
Notes
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Reaction equation

HRID 1516248 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=6.4 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-e445926c33b84bfbacf270b34e477d89
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08227473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes