Hydrochloric Acid → Hydrochloric Acid

HRID 2404207Notes

Reaction equation

HRID 2404207 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH:19]3[CH2:24][CH2:23][CH:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:21][CH2:20]3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.O1CCOCC1.CCOCC.[ClH:40]>>[C:25]([CH:22]1[CH2:23][CH2:24][CH:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:17][CH2:16]3)[CH2:20][CH2:21]1)([CH3:28])([CH3:26])[CH3:27].[ClH:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 669267656-(4-tert-Butyl-cyclohexyloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 98%HCID 679606146-(4-tert-Butyl-cyclohexyloxy)-1,2,3,4-tetrahydro-isoquinoline

Procedure

A solution of 6-(4-tert-butyl-cyclohexyloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.89 g, 2.3 mmol) in 4 M of HCl in 1,4-dioxane (10 mL, 40 mmol) and ether (40 mL) was stirred at room temperature for 3 hrs to form white precipitate. The solid was collected by filtration to give desired product as HCl salt (0.73 g, yield: 98%). (400 MHz, DMSO) δ 7.09 (d, 1H), 6.81 (d, 1H), 6.80 (s, 1H), 4.20 (m, 1H), 4.14 (m, 2H), 3.31 (m, 2H), 2.95 (t, 2H), 2.09 (d, 2H), 1.77 (d, 2H), 1.27 (m, 2H), 1.20-0.98 (m, 3H), 0.85 (s, 9H).

Workup

  1. customto form white precipitate
  2. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-81e5e9aab5804964ba4982688e3b1ad8
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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