Triethylamine → HCID 11078903, compound

HRID 1489194Notes

Reaction equation

HRID 1489194 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:24]([O:26]CC)=[O:25])([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(C1(N2CCCCC2=O)CCNCC1)=O)C.C(OC(ON1C(=O)CCC1=O)=O)C1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:24]([OH:26])=[O:25])([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 11010525HCID 11010525, compoundHCID 11101150HCID 11101150, compound

Product 1

HCID 11078903HCID 11078903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Benzyloxycarbonyl-4-(ethoxycarbonyl)-4-(2-oxopiperidino)-piperidine. 4-(Ethoxycarbonyl)-4-(2-oxopiperidino)piperidine (9.0 g) in dichloromethane (25 mL) was added to a solution of N-(benzyloxycarbonyloxy)succinimide (8.8 g) and triethylamine (5.4 mL) in dichloromethane (150 mL). After 1.5 hours, the reaction mixture was washed successively with 1.0N hydrochloric acid and saturated aqueous sodium bicarbonate. The separated organic layer was dried and evaporated to give the title compound (11.6 g) as a light yellow solid; MS: m/z=389(M+1); NMR (CDCl3 /CF3COOH): 7.37 (m,5), 5.16 (s,2), 4.28 (q,2, J=7.1), 4.09 (m,2), 3.40 (m,2), 3.28 (m,2), 2.53 (m,2), 2.34 (m,2), 1.83 (m,6), 1.30 (t,3, J=7.1).

Workup

  1. washthe reaction mixture was washed successively with 1.0N hydrochloric acid and saturated aqueous sodium bicarbonate
  2. customThe separated organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-9cb28b698dcc42a29091d6c7847cccb4
Source dataset
uspto-grants-1997_10
Patent number
US05677317

Reaction notes

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